3-amino-1,2-benzisothiazole compounds for combating animal pest II

ABSTRACT

The invention provides 3-amino-1,2-benzisothiazole compounds of formula (I) wherein n, R 1 , R 2 , R 3 , R 4  and A are defined as in the description. The invention provides further agricultural compositions comprising an amount of at least one compound of the formula (I) or an enantiomer, diastereomer or salt thereof; the use of a compound of formula (I) or an enantiomer, diastereomer or salt thereof for combating animal pests; a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one compound of the formula (I) or an enantiomer, diastereomer or salt thereof; a method for protecting crops from attack or infestation by animal pests, which comprises contacting a crop with a pesticidally effective amount of at least one compound of the formula (I) or an enantiomer, diastereomer or salt thereof; a method for the protection of seeds from soil insects and of the seedlings&#39; roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one compound of the formula (I), or the enantiomers, diastereomers or salts thereof; and seeds comprising a compound of the formula I or an enantiomer, diastereomer or salt thereof.

This application is a National Stage application of InternationalApplication No. PCT/EP2008/050337 filed Jan. 14, 2008, which claims thebenefit of U.S. Provisional Application No. 60/886,761, filed Jan. 26,2007, the entire contents of which is hereby incorporated herein byreference.

The present invention relates to 3-amino-1,2-benzisothiazole compoundsand to their isomeric imino derivatives, as well as to the enantiomers,diastereomers and salts thereof and to compositions comprising suchcompounds. The invention also relates to the use of the3-amino-1,2-benzisothiazole compounds, of their salts or of compositionscomprising them for combating animal pests. Furthermore the inventionrelates also to methods of applying such compounds.

Animal pests destroy growing and harvested crops and attack woodendwelling and commercial structures, causing large economic loss to thefood supply and to property. While a large number of pesticidal agentsare known, due to the ability of target pests to develop resistance tosaid agents, there is an ongoing need for new agents for combatinganimal pests. In particular, animal pests such as insects and acaridaeare difficult to be effectively controlled.

It is therefore an object of the present invention to provide compoundshaving a good pesticidal activity, especially against difficult tocontrol insects and acaridae.

It has been found that these objects are solved by3-amino-1,2-benzisothiazole derivatives of the general formula I:

wherein

-   n is 0, 1 or 2;

-   A is A¹, A², A³ or A⁴ and wherein-   m is 0 or 1;-   q is 0, 1 or 2;-   R⁵, R⁶, R⁸ are independently from each other selected from    C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₃-C₁₀-cycloalkyl,    phenyl, naphtyl and 5- or 6-membered heteroaromatic or 3 to    7-membered saturated or partially unsaturated heterocyclic groups    containing 1, 2, 3 or 4 unsubstituted or substituted heteroatoms    selected from O, S, SO, SO₂, N, NH or N—C₁-C₆-alkyl as ring members,    wherein the heterocyclic groups may additionally contain 1, 2 or 3    CO groups as ring members, and wherein the aliphatic radicals and    the ring members of the cyclic groups may be unsubstituted,    partially or fully halogenated and/or may carry one or more    radicals, independently of one another selected from the group    consisting of CN, NO₂, NH₂, C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl,    C₁-C₁₀-alkoxy, C₁-C₁₀-haloalkoxy, C₁-C₁₀-alkylthio,    C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl, C₁-C₁₀-haloalkoxy,    C₁-C₁₀-haloalkylthio, C₁-C₁₀-alkoxycarbonyl, (C₁-C₁₀-alkyl)amino,    di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl and phenyl, it being    possible for phenyl to be unsubstituted, partially or fully    halogenated and/or to carry one or more substituents, independently    of one another selected from the group consisting of C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;-   R⁷ or R⁹ is selected from hydrogen, C(═O)—R^(c), C₁-C₆-alkoxy,    C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₃-C₁₀-cycloalkyl,    phenyl, naphtyl and 5- or 6-membered heteroaromatic or 3 to    7-membered saturated or partially unsaturated heterocyclic groups    containing 1, 2, 3 or 4 unsubstituted or substituted heteroatoms    selected from O, S, SO, SO₂, N, NH or N—C₁-C₆-alkyl as ring members,    wherein the heterocyclic groups may additionally contain 1, 2 or 3    CO groups as ring members, wherein the aliphatic radicals may be    unsubstituted, partially or fully halogenated and/or may carry one    or more radicals, independently of one another selected from the    group consisting of CN, NO₂, C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl    C₃-C₁₀-cycloalkyl and phenyl, it being possible for phenyl to be    unsubstituted, partially or fully halogenated and/or to carry one or    more substituents, independently of one another selected from the    group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and    C₁-C₄-haloalkoxy, wherein the ring members of the cyclic groups may    be unsubstituted, partially or fully halogenated and/or may carry    one or more radicals, independently of one another selected from the    group consisting of CN, NO₂, NH₂, C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl,    C₁-C₁₀-alkoxy, C₁-C₁₀-haloalkoxy, C₁-C₁₀-alkylthio,    C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl, C₁-C₁₀-haloalkoxy,    C₁-C₁₀-haloalkylthio, C₁-C₁₀-alkoxycarbonyl, (C₁-C₁₀-alkyl)amino,    di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl and phenyl, it being    possible for phenyl to be unsubstituted, partially or fully    halogenated and/or to carry one or more substituents, independently    of one another selected from the group consisting of C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;    or-   R⁵ and R⁶ form together with the sulfur atom they are bound to a    saturated, partially or fully unsaturated 4 to 10-membered    heterocyclic ring, optionally substituted by 1, 2, 3 or 4 radicals    selected from C₁-C₆-alkyl and halogen, wherein the ring may contain,    in addition to the sulfur atom, 1, 2 or 3 heteroatoms selected from    the group consisting of N, O, S, CO, SO, SO₂ and N—R^(e);    or-   R⁷ and R⁸ form together with the sulfur atom and the nitrogen atom    they are bound to a saturated, partially or fully unsaturated 4 to    10-membered heterocyclic ring, optionally substituted by 1, 2, 3 or    4 radicals selected from C₁-C₆-alkyl and halogen, wherein the ring    may contain, in addition to the sulfur and nitrogen atom, 1, 2 or 3    heteroatoms selected from the group consisting of N, O, S, CO, SO,    SO₂ and N—R^(e);-   R¹⁰ is selected dependently from R⁹, wherein    when R⁹ is selected from substituents other than hydrogen and    COR^(C),    -   R¹⁰ is selected from substituents as defined for R¹² below;        or wherein        when R⁹ is selected from hydrogen or COR^(C),-   R¹⁰ is selected from saturated, partially or fully unsaturated or    aromatic 5- to 7-membered heterocyclic groups containing 1, 2, 3 or    4 heteroatoms selected from O, CO, S, SO₂, N, NH or N—C₁-C₆-alkyl,    wherein the ring members of the heterocyclic rings may be    unsubstituted, partially or fully halogenated and/or may carry one    or more radicals, independently of one another each selected from    the group consisting of CN, OH, NO₂, NH₂, C₁-C₁₀-alkyl,    C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy, C₁-C₁₀-haloalkoxy,    C₁-C₁₀-alkylthio, C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl,    C₁-C₁₀-haloalkylthio, C₁-C₁₀-alkoxycarbonyl, (C₁-C₁₀-alkyl)amino,    di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl, phenyl, 5- or 6-membered    heteroaromatic rings and aromatic 8-, 9- or 10-membered fused    heterobicyclic ring systems containing 1, 2, 3 or 4 heteroatoms    selected from O, CO, S, SO₂, N, NH or N—C₁-C₆-alkyl, it being    possible for each of the aromatic or heteroaromatic rings to be    unsubstituted, partially or fully halogenated and/or to carry one or    more substituents, independently of one another selected from the    group consisting of C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy,    C₁-C₁₀-haloalkoxy, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    C₂-C₁₀-haloalkenyl, C₂-C₁₀-haloalkynyl, CN, NO₂, NH₂,    C₁-C₁₀-alkylthio, C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl,    C₁-C₁₀-haloalkylthio, C₂-C₁₀-alkoxycarbonyl,    C₁-C₁₀-alkylaminocarbonyl, C₁-C₁₀-dialkylaminocarbonyl,    (C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl,    C₃-C₁₀-halocycloalkyl, C₃-C₁₀-cycloalkylamino and    C₂-C₁₀-alkylcarbonyl;-   R¹¹ is selected from hydrogen, C(═O)—R^(c), C₁-C₁₀-alkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₁₀-alkoxy and C₃-C₁₀-cycloalkyl,    wherein the carbon atoms-of all mentioned radicals may be    unsubstituted, partially or fully halogenated and/or may carry one    or more radicals, independently of one another each selected from    the group consisting of CN, OH, NO₂, NH₂, C₁-C₆-alkyl,    C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy, C₁-C₁₀-alkylthio,    C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl, C₁-C₁₀-haloalkoxy,    C₁-C₁₀-haloalkylthio, C₁-C₁₀-alkoxycarbonyl, (C₁-C₁₀-alkyl)amino,    di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl and phenyl, it being    possible for phenyl to be unsubstituted, partially or fully    halogenated and/or to carry one or more substituents, independently    of one another selected from the group consisting of C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;-   R¹² is selected from OR^(d), NR^(a)R^(b), C₁-C₁₀-alkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₃-C₁₀-cycloalkyl, phenyl, naphtly    and saturated, partially or fully unsaturated or aromatic 5- to    7-membered heterocyclic groups containing 1, 2, 3 or 4 heteroatoms    selected from O, CO, S, SO₂, N, NH or N—C₁-C₆-alkyl, wherein the    carbon atoms-of all mentioned radicals and the ring members of the    heterocyclic rings may be unsubstituted, partially or fully    halogenated and/or may carry one or more radicals, independently of    one another each selected from the group consisting of CN, OH, NO₂,    NH₂, C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy,    C₁-C₁₀-haloalkoxy, C₁-C₁₀-alkylthio, C₁-C₁₀-alkylsulfinyl,    C₁-C₁₀-alkylsulfonyl, C₁-C₁₀-haloalkylthio, C₁-C₁₀-alkoxycarbonyl,    (C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl,    phenyl, 5- or 6-membered heteroaromatic rings and aromatic 8-, 9- or    10-membered fused heterobicyclic ring systems containing 1, 2, 3 or    4 heteroatoms selected from O, CO, S, SO₂, N, NH or N—C₁-C₆-alkyl,    it being possible for each of the aromatic or heteroaromatic rings    to be unsubstituted, partially or fully halogenated and/or to carry    one or more substituents, independently of one another selected from    the group consisting of C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl,    C₁-C₁₀-alkoxy, C₁-C₁₀-haloalkoxy, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    C₂-C₁₀-haloalkenyl, C₂-C₁₀-haloalkynyl, CN, NO₂, NH₂,    C₁-C₁₀-alkylthio, C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl,    C₁-C₁₀-haloalkylthio, C₁-C₁₀-alkoxycarbonyl,    C₁-C₁₀-alkylaminocarbonyl, C₁-C₁₀-dialkylaminocarbonyl,    (C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl,    C₃-C₁₀-halocycloalkyl, C₃-C₁₀-cycloalkylamino and    C₁-C₁₀-alkylcarbonyl;-   R¹ is selected from CN, NO₂, NH₂, azido, halogen, sulfonylamino,    sulfenylamino, sulfinylamino, C(═O)R^(c), C₁-C₁₀-alkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₃-C₁₀-cycloalkyl, C₁-C₁₀-alkoxy,    C₁-C₁₀-alkylthio, (C₁-C₁₀-alkyl)amino, di(C₁-C₁₀-alkyl)amino,    C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfenyl and C₁-C₁₀-alkylsulfonyl,    wherein the carbon atoms of the C₃-C₁₀-cycloalkyl and the mentioned    aliphatic radicals may be unsubstituted, partially or fully    halogenated and/or may carry one or more radicals, selected from the    group consisting of CN, NO₂, NH₂, C₁-C₁₀-alkoxy, C₁-C₁₀-alkylthio,    C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl, C₁-C₁₀-haloalkoxy,    C₁-C₁₀-haloalkylthio, (C₁-C₁₀-alkoxy)carbonyl, (C₁-C₁₀-alkyl)amino,    di(C₁-C₁₀-alkyl)amino, C₃-C₈-cycloalkyl and phenyl, it being    possible for phenyl to be unsubstituted, partially or fully    halogenated and/or to carry one or more substituents, independently    of one another selected from the group consisting of C₁-C₁₀-alkyl,    C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy and C₁-C₁₀-haloalkoxy;-   R², R³ and R⁴ are independently from each other selected from    hydrogen, halogen, azido, COR^(C), CN, NO₂, NH₂, C₁-C₁₀-alkyl,    C₃-C₁₀-cycloalkyl, C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy,    C₁-C₁₀-alkylthio, C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl,    C₁-C₁₀-haloalkoxy, C₁-C₁₀-haloalkylthio, C₂-C₁₀-alkenyl,    C₂-C₁₀-alkynyl, (C₁-C₁₀-alkyl)amino, di(C₁-C₁₀-alkyl)amino,    sulfonyl, sulfonylamino, sulfenylamino and sulfanylamino;    and wherein-   R^(a) and R^(b) are selected independently from each other from the    group consisting of hydrogen, C₁-C₁₀-alkyl, C₃-C₁₀-cycloalkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, aryl and aromatic, saturated,    partially or fully unsaturated heterocyclic rings, and wherein the    carbon atoms of all mentioned radicals may be unsubstituted or    partially or fully substituted by halogen or C₁-C₁₀-alkyl;-   R^(c) is selected from the group consisting of NH₂, C₁-C₁₀-alkyl,    C₁-C₁₀-alkoxy, C₁-C₁₀-alkylamino, di(C₁-C₁₀-alkyl)amino, aryl and    saturated, partially unsaturated or aromatic 3- to 7-membered    heterocyclic ring, which may contain as ring members 1, 2 or 3    unsubstituted or substituted heteroatoms selected from the group    consisting of O, S, SO, SO₂, N, NH and N—C₁-C₆-alkyl, and wherein    the carbon atoms of all mentioned radicals may be unsubstituted or    partially or fully substituted by halogen or C₁-C₁₀-alkyl;-   R^(d) is selected from the group consisting of hydrogen,    C₁-C₁₀-alkyl, C₃-C₁₀-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    aryl and aromatic, saturated, partially or fully unsaturated    heterocyclic rings;-   R^(e) is hydrogen or C₁-C₁₀-alkyl;    or the enantiomers, diastereomers or salts thereof.

Depending on the substitution pattern, the compounds of formula I cancontain one or more chiral centers, in which case they are present asenantiomer or diastereomer mixtures. Subject matter of this inventionare not only compositions containing these mixtures but also thosecontaining the pure enantiomers or diastereomers.

Some similar compounds to formula I have been described inter alia inDE-A 1915387, WO 03/87072, JP-A 06220030, DE-A 1670920 and DE-A 1545842.Benzoisothiazoles useful for treating or preventing HCV infection can befound in WO2006/091858. However, an insecticidal, acaricidal ornematicidal activity of compounds of formula I has not been disclosedyet.

Amino- and amino-acylated1,2-benzisothiazole compounds have beendescribed by Drabek for an insecticidal activity in EP-A 207891, EP-A191734, DE-A 3544436, EP-A 138762, EP-A 133418 and EP-A 110829, or3-Amidinobenzisothiazole 1,1-dioxides for same use in EP-A 86748. JP-A01319467 describes the preparation of N-acylated amino-benzisothiazolesand their 1,2-dioxyde derivatives as active ingredients for insecticidalpurposes. Sulfonyl compounds and aphicidal compositions based onmono-substituted 3-amino-1,2-benzisothiazole-1,1-dioxyde derivativeshave been described in EP-A 0033984. The latter EP-A 33984 discloses2-cyanobenzene sulfonamides having aphicidal activity. Their activity,however, is not satisfactory. Similar compounds to EP-A 33984 aredescribed in WO 2005/035486, in unpublished international applicationPCT/EP2006/068469 and in unpublished U.S. application 60/787,809.

The compounds of the formula I, and their agriculturally acceptablesalts are highly active against animal pest, i.e. harmful arthropodesand nematodes, especially against difficult to control insects andacaridae.

Accordingly, the present invention relates to3-amino-1,2-benzisothiazole compounds of the general formula I and totheir agriculturally useful salts.

Moreover, the present invention relates to:

-   -   agricultural compositions comprising an amount of at least one        compound of the formula I or an enantiomer, diastereomer or salt        thereof;    -   the use of a compound of formula I or an enantiomer,        diastereomer or salt thereof for combating animal pests;    -   a method of combating animal pests which comprises contacting        the animal pests, their habit, breeding ground, food supply,        plant, seed, soil, area, material or environment in which the        animal pests are growing or may grow, or the materials, plants,        seeds, soils, surfaces or spaces to be protected from animal        attack or infestation with a pesticidally effective amount of at        least one compound of the formula I or an enantiomer,        diastereomer or salt thereof;    -   a method for protecting crops from attack or infestation by        animal pests, which comprises contacting a crop with a        pesticidally effective amount of at least one compound of the        formula I or an enantiomer, diastereomer or salt thereof;    -   a method for the protection of seeds from soil insects and of        the seedlings' roots and shoots from soil and foliar insects        comprising contacting the seeds before sowing and/or after        pregermination with at least one compound of the formula I, or        the enantiomers, diastereomers or salts thereof;    -   seeds comprising a compound of the formula I or an enantiomer,        diastereomer or salt thereof.

Salts of the compounds of the formula I are preferably agriculturallyacceptable salts. They can be formed in a customary method, e.g. byreacting the compound with an acid of the anion in question if thecompound of formula I has a basic functionality or by reacting an acidiccompound of formula I with a suitable base.

Suitable agriculturally useful salts are especially the salts of thosecations or the acid addition salts of those acids whose cations andanions, respectively, do not have any adverse effect on the action ofthe compounds according to the present invention. Suitable cations arein particular the ions of the alkali metals, preferably lithium, sodiumand potassium, of the alkaline earth metals, preferably calcium,magnesium and barium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium (NH₄ ⁺) andsubstituted ammonium in which one to four of the hydrogen atoms arereplaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl orbenzyl. Examples of substituted ammonium ions comprise methylammonium,isopropylammonium, dimethylammonium, diisopropylammonium,trimethylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethylammonium,2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium,benzyltrimethylammonium and benzyltriethylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, phosphate, nitrate, hydrogen carbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting the compounds of the formulae Iwith an acid of the corresponding anion, preferably of hydrochloricacid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The organic moieties mentioned in the above definitions of the variablesare—like the term halogen—collective terms for individual listings ofthe individual group members. The prefix C_(n)-C_(m) indicates in eachcase the possible number of carbon atoms in the group.

“Halogen” will be taken to mean fluoro, chloro, bromo and iodo.

The term “partially or fully halogenated” will be taken to mean that 1or more, e.g. 1, 2, 3, 4 or 5 or all of the hydrogen atoms of a givenradical have been replaced by a halogen atom, in particular by fluorineor chlorine.

The term “C_(n)-C_(m)-alkyl” as used herein (and also inC_(n)-C_(m)-alkylamino, di-C_(n)-C_(m)-alkylamino,C_(n)-C_(m)-alkylaminocarbonyl, di-(C_(n)-C_(m)-alkylamino)carbonyl,C_(n)-C_(m)-alkylthio, C_(n)-C_(m)-alkylsulfinyl andC_(n)-C_(m)-alkylsulfonyl) refers to a branched or unbranched saturatedhydrocarbon group having n to m, e.g. 1 to 10 carbon atoms, preferably 1to 6 carbon atoms, for example methyl, ethyl, propyl, 1-methylethyl,butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl,2-ethylhexyl, nonyl and decyl and their isomers. C₁-C₄-alkyl means forexample methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl.

The term “C_(n)-C_(m)-haloalkyl” as used herein (and also inC_(n)-C_(m)-haloalkylsulfinyl and C_(n)-C_(m)-haloalkylsulfonyl) refersto a straight-chain or branched alkyl group having n to m carbon atoms,e.g. 1 to 10 in particular 1 to 6 carbon atoms (as mentioned above),where some or all of the hydrogen atoms in these groups may be replacedby halogen atoms as mentioned above, for example C₁-C₄-haloalkyl, suchas chloromethyl, bromomethyl, dichloromethyl, trichloromethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl andthe like. The term C₁-C₁₀-haloalkyl in particular comprisesC₁-C₂-fluoroalkyl, which is synonym with methyl or ethyl, wherein 1, 2,3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such asfluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl andpentafluoromethyl.

Similarly, “C_(n)-C_(m)-alkoxy” and “C_(n)-C_(m)-alkylthio” (orC_(n)-C_(m)-alkylsulfenyl, respectively) refer to straight-chain orbranched alkyl groups having n to m carbon atoms, e.g. 1 to 10, inparticular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bondedthrough oxygen or sulfur linkages, respectively, at any bond in thealkyl group. Examples include C₁-C₄-alkoxy such as methoxy, ethoxy,propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy,further C₁-C₄-alkylthio such as methylthio, ethylthio, propylthio,isopropylthio, and n-butylthio.

Accordingly, the terms “C_(n)-C_(m)-haloalkoxy” and“C_(n)-C_(m)-haloalkylthio” (or C_(n)-C_(m)-haloalkylsulfenyl,respectively) refer to straight-chain or branched alkyl groups having nto m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbonatoms (as mentioned above) bonded through oxygen or sulfur linkages,respectively, at any bond in the alkyl group, where some or all of thehydrogen atoms in these groups may be replaced by halogen atoms asmentioned above, for example C₁-C₂-haloalkoxy, such as chloromethoxy,bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy,difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy,dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy,1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy,2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy and pentafluoroethoxy, furtherC₁-C₂-haloalkylthio, such as chloromethylthio, bromomethylthio,dichloromethylthio, trichloromethylthio, fluoromethylthio,difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio,dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio,1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio andpentafluoroethylthio and the like. Similarly the termsC₁-C₂-fluoroalkoxy and C₁-C₂-fluoroalkylthio refer to C₁-C₂-fluoroalkylwhich is bound to the remainder of the molecule via an oxygen atom or asulfur atom, respectively.

The term “C₂-C_(m)-alkenyl” as used herein intends a branched orunbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or2 to 6 carbon atoms and a double bond in any position, such as ethenyl,1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term “C₂-C_(m)-alkynyl” as used herein refers to a branched orunbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or2 to 6 carbon atoms and containing at least one triple bond, such asethynyl, propynyl, 1-butynyl, 2-butynyl, and the like.

The term “C₁-C₄-alkoxy-C₁-C₄-alkyl” as used herein refers to alkylhaving 1 to 4 carbon atoms, e.g. like specific examples mentioned above,wherein one hydrogen atom of the alkyl radical is replaced by anC₁-C₄-alkoxy group.

The term “C₁-C₄-alkylthio-C₁-C₄-alkyl” as used herein refers to alkylhaving 1 to 4 carbon atoms, wherein one hydrogen atom of the alkylradical is replaced by a C₁-C₄-alkylthio group.

The term “C₃-C_(m)-cycloalkyl” as used herein refers to a monocyclic 3-to m-membered saturated cycloaliphatic radicals, e.g. cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl andcyclodecyl.

The term “aryl” as used herein refers to an aromatic hydrocarbon radicalsuch as naphthyl or in particular phenyl.

The term “aryl-C₁-C₄-alkyl” as used herein refers to an aromatichydrocarbon radical, which is bound to the remainder of the molecule viaa C₁-C₄-alkylene group, examples comprise benzyl, 1-phenylethyl or2-phenylethyl.

The term “3- to 7” or “5- to 7”-“membered heterocyclyl” or “memberedheterocyclic group” as used herein (and also in“heterocyclyl-C₁-C₄-alkyl”) refers to a saturated, fully or partiallyunsaturated or aromatic heterocyclic radicals having 3 to 7 or 5 to 7ring members, wherein 1, 2 or 3 ring members are heteroatoms selectedfrom O, N and S or heteroatom groups, selected from S═O, S(O)₂ or N—Rwith R being H or alkyl. Examples for non-aromatic rings includeazetidiyl, pyrrolidinyl, pyrazolinyl, imidazolinyl, pyrrolinyl,pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydrofuranyl,1,3-dioxolanyl, dioxolenyl, thiolanyl, dihydrothienyl, oxazolidinyl,isoxazolidinyl, oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl,thiazolidinyl, isothiazolidinyl, oxathiolanyl, piperidinyl, piperazinyl,pyranyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, thiopyranyl,dihydrothiopyranyl, tetrahydrothiopyranyl, morpholinyl, thiazinyl andthe like. Examples for aromatic rings are listed in the followingparagraph.

The term “3- to 7” or “5- to 7”-“membered heteroaryl” or “memberedheteroaromatic group” as used herein (and also in“heteroaryl-C₁-C₄-alkyl”) refers to an aromatic heterocyclic radicalhaving 3 to 7 or 5 to 7 ring members, wherein 1, 2 or 3 ring members areheteroatoms selected from O, N and S or heteroatom groups, selected fromS═O, S(O)₂ or N—R with R being H or alkyl. Examples for monocyclic 3- to7-membered heteroaromatic rings include triazinyl, pyrazinyl, pyrimidyl,pyridazinyl, pyridyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl,triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl,isothiazolyl and isoxazolyl.

The terms “heterocyclyl-C₁-C₄-alkyl” as used herein refer to aromaticand non-aromatic saturated, fully or partially unsaturated heterocyclicand the terms “heteroaryl-C₁-C₄-alkyl” as used herein refer to aromaticradicals, which are both bound to the remainder of the molecule via aC₁-C₄-alkylene group.

Preferences

With respect to the use according to the invention of the3-amino-1,2-benzisothiazole compounds of formula I, particularpreference is given to the following meanings of the substituents andvariables, in each case on their own or in combination:

Preference is given to 3-amino-1,2 benzisothiazole compounds of formulaI, wherein A is A³.

Preferred are 3-amino-1,2 benzisothiazole compounds of formula I,wherein n is 2 and A is selected from A¹ or A².

Preferred are especially 3-amino-1,2 benzisothiazole compounds offormula I, wherein n is 1 and A is A³.

Preferred are also 3-amino-1,2 benzisothiazole compounds of formula I,wherein n is 0 and A is A³.

Preference is given to 3-amino-1,2 benzisothiazole compounds of formulaI, wherein R¹ is selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.

Preference is especially given to 3-amino-1,2 benzisothiazole compoundsof formula I, wherein R¹ is selected from halogen, C₁-C₆-alkoxy andC₁-C₆-haloalkoxy.

Most preferred are 3-amino-1,2 benzisothiazole compounds of formula I,wherein R¹ is selected from fluoro, chloro, difluoromethoxy,dichloromethoxy, trifluoromethoxy or trichloromethoxy.

Preference is given to 3-amino-1,2 benzisothiazole compounds of formulaI, wherein R², R³ and R⁴ are independently from one another selectedfrom the group consisting of hydrogen and F, Cl, Br or J.

Preference is especially given to 3-amino-1,2 benzisothiazole compoundsof formula I, wherein R², R³ and R⁴ are independently from one anotherselected from hydrogen or fluoro.

Most preferred are 3-amino-1,2 benzisothiazole compounds of formula I,wherein R², R³ and R⁴ are hydrogen.

Preference is given to 3-amino-1,2 benzisothiazole compounds of formulaI, wherein when A is selected from A¹ and R⁵ and R⁶ form together withthe sulfur atom they are bound to a saturated, partially or fullyunsaturated or aromatic 5, 6 or 7-membered heterocyclic ring, optionallysubstituted by 1, 2, 3 or 4 radicals selected from C₁-C₅-alkyl andhalogen, which may contain, in addition to the sulfur atom, 1, 2 or 3unsubstituted or substituted heteroatoms selected from O, CO, S, SO,SO₂, N, NH, or N—C₁-C₆-alkyl.

Preference is given to 3-amino-1,2 benzisothiazole compounds of formulaI, wherein when A is selected from A² and R⁷ and R⁸ form together withthe sulfur atom and the nitrogen atom they are bound to a saturated,partially or fully unsaturated or aromatic 5, 6 or 7-memberedheterocyclic ring, optionally substituted by 1, 2, 3 or 4 radicalsselected from C₁-C₅-alkyl and halogen, which may contain, in addition tothe sulfur atom, 1, 2 or 3 unsubstituted or substituted heteroatomsselected from O, CO, S, SO, SO₂, N, NH, or N—C₁-C₆-alkyl.

Preference is especially given to 3-amino-1,2 benzisothiazole compoundsof formula I, wherein A is A¹ or A² and R⁵ and R⁶ or respectively R⁷ andR⁸ are independently from one another selected from C₁-C₆-alkyl orC₃-C₁₀-cycloalkyl, which both may be unsubstituted, partially or fullyhalogenated.

Most preferred are 3-amino-1,2 benzisothiazole compounds of formula I,wherein A is A¹ or A² and R⁵ and R⁶ or respectively R⁷ and R⁸ areindependently from one another selected from methyl, ethyl, n-propyl,i-propyl, which may be unsubstituted, partially or fully halogenated.

Preference is given to 3-amino-1,2 benzisothiazole compounds of formulaI, wherein A is A³, R⁹ is C₁-C₆-alkyl and R¹⁰ is selected fromC₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₃-C₁₀-cycloalkyl and phenyl, wherein the radicals may be unsubstituted,partially or fully halogenated and/or may carry one or more radicals,independently of one another each selected from the group consisting ofCN, NO₂, NH₂, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio,C₁-C₆-alkoxycarbonyl, (C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino,C₃-C₁₀-cycloalkyl and phenyl, it being possible for phenyl to beunsubstituted, partially or fully halogenated and/or to carry one ormore substituents, independently of one another selected from the groupconsisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy.

Preference is also given to 3-amino-1,2 benzisothiazole compounds offormula I, wherein A is A³, R⁹ is selected from hydrogen or C₁-C₆-alkyland R¹⁰ is selected from pyridine, pyrazine, pyrimidine, pyrazole,imdidazole, triazole, thiophene, thiazole, oxazole, furan, isothiazole,isoxazole, piperidine, tetrahydrofuran, dihydrofuran, thiolan,dihydrothiophen, pyrrolidine, dihydropyrrol, dihydropyrazole,dihydrooxazole, dihydrothiazole, oxathiolan or oxazolidine, each ringoptionally substituted with 1 to 3 substituents independently of oneanother selected from the group consisting of CN, OH, NO₂, NH₂,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylthio, C₁-C₆-alkoxycarbonyl, (C₁-C₁₀-alkyl)amino,di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl, phenyl and 5- or 6-memberedheteroaromatic ring, it being possible for the aromatic or heteraromaticrings to be unsubstituted, partially or fully halogenated and/or tocarry one or more substituents, independently of one another selectedfrom the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkenyl,C₂-C₆-haloalkynyl, CN, NO₂, NH₂, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylthio, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylaminocarbonyl, C₃-C₆-dialkylaminocarbonyl,(C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl,C₃-C₁₀-halocycloalkyl, C₃-C₁₀-cycloalkylamino, C₂-C₆-alkylcarbonyl.

Preference is especially given to 3-amino-1,2 benzisothiazole compoundsof formula I, wherein A is A³, R⁹ is selected from hydrogen orC₁-C₆-alkyl and R¹⁰ is selected from pyridine, pyrazine, pyrimidine,pyrazole, imdidazole, triazole, thiophene, thiazole, oxazole, furan,isothiazole, isoxazole, piperidine, tetrahydrofuran, dihydrofuran,thiolan, dihydrothiophen, pyrrolidine, dihydropyrrol, dihydropyrazole,dihydrooxazole, dihydrothiazole, oxathiolan or oxazolidine, each ringoptionally substituted with one to three substituents independently ofone another selected from the group consisting of CN, OH, NO₂, NH₂,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylthio, C₁-C₆-alkoxycarbonyl, (C₁-C₁₀-alkyl)amino,di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl, phenyl, pyridine, pyrimidine,thiophene, isooxazol and isothiazol, it being possible for the aromaticor heteroaromatic rings to be unsubstituted, partially or fullyhalogenated and/or to carry one or more substituents, independently ofone another selected from the group consisting of C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, cyano, nitro,amino, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl andC₁-C₆-haloalkylthio.

Preference is given to 3-amino-1,2 benzisothiazole compounds of formulaI, wherein R¹ is selected from halogen, C₁-C₆-alkoxy or C₁-C₆-haloalkoxyand R², R³ and R⁴ are independently of one another selected from thegroup consisting of hydrogen, F, Cl, Br or J.

Preference is especially given 3-amino-1,2 benzisothiazole compounds offormula I, wherein R¹ is selected from halogen, C₁-C₆-alkoxy orC₁-C₆-haloalkoxy and R², R³ and R⁴ are hydrogen.

Preference is given to 3-amino-1,2 benzisothiazole compounds of formulaI, wherein A is A¹, R¹ is selected from C₁-C₆-alkoxy orC₁-C₆-haloalkoxy, R², R³ and R⁴ are independently of one anotherselected from the group consisting of hydrogen, F, Cl, Br or J and R⁵and R⁶ are selected independently from each other from C₁-C₄-alkyl orform together with the sulfur atom as sole heteroatom a 5 or 6 memberedsaturated heterocyclic ring.

Preference is given to 3-amino-1,2 benzisothiazole compounds of formulaI, wherein A is A³, R¹ is selected from C₁-C₆-alkoxy orC₁-C₆-haloalkoxy, R², R³ and R⁴ are independently of one anotherselected from the group consisting of hydrogen, F, Cl, Br or J, R⁹ isC₁-C₆-alkyl and R¹⁰ is selected from C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-alkoxy and C₃-C₁₀-cycloalkyl, wherein the carbonatoms-of all mentioned radicals may be unsubstituted, partially or fullyhalogenated and/or may carry one or more radicals, independently of oneanother each selected from the group consisting of CN, NO₂, NH₂,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio, C₁-C₆-alkoxycarbonyl,(C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl phenyl ora 5- or 6-membered heteroaromatic ring it being possible for each ringto be unsubstituted, partially or fully halogenated and/or to carry oneor more substituents, independently of one another selected from thegroup consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkenyl,C₂-C₆-haloalkynyl, CN, NO₂, NH₂, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylthio, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylaminocarbonyl, C₃-C₆-dialkylaminocarbonyl,(C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl,C₃-C₁₀-halocycloalkyl, C₃-C₁₀-cycloalkylamino, C₂-C₆-alkylcarbonyl.

Preference is especially given to 3-amino-1,2 benzisothiazole compoundsof formula I, wherein A is A³, n is 0, R¹ is selected from C₁-C₆-alkoxyor C₁-C₆-haloalkoxy, R², R³ and R⁴ are hydrogen, R⁹ is C₁-C₆-alkyl andR¹⁰ is selected from C₁-C₆-alkyl, C₃-C₁₀-cycloalkyl or phenyl, whereinthe carbon atoms or the carbocyclic ring of the radicals may beunsubstituted, partially or fully halogenated and/or may carry one ormore substituents, independently of one another selected from the groupconsisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkenyl,C₂-C₆-haloalkynyl, CN, NO₂, NH₂, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylthio.

Most preferred are 3-amino-1,2 benzisothiazole compounds of formula I,wherein A is A³, n is 0, R¹ is selected from C₁-C₆-alkoxy orC₁-C₆-haloalkoxy, R², R³ and R⁴ are hydrogen, R⁹ is selected fromhydrogen or C₁-C₆-alkyl and R¹⁰ is selected from pyridine, pyrazine,pyrimidine, pyrazole, imdidazole, triazole, thiophene, thiazole,oxazole, furan, isothiazole, isoxazole, piperidine, tetrahydrofuran,dihydrofuran, thiolan, dihydrothiophen, pyrrolidine, dihydropyrrol,dihydropyrazole, dihydrooxazole, dihydrothiazole, oxathiolan oroxazolidineeach ring optionally substituted with one to threesubstituents independently of one another selected from the groupconsisting of CN, OH, NO₂, NH₂, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylthio, C₁-C₆-alkoxycarbonyl,(C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl, phenyland 5- or 6-membered heteroaromatic ring, it being possible for thearomatic and heteroaromatic rings to be unsubstituted, partially orfully halogenated and/or to carry one or more substituents,independently of one another selected from the group consisting ofC₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, CN,NO₂, NH₂, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylthio, C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylaminocarbonyl,C₃-C₆-dialkylaminocarbonyl, (C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino,C₃-C₁₀-cycloalkyl, C₃-C₁₀-halocycloalkyl, C₃-C₁₀-cycloalkylamino,C₂-C₆-alkylcarbonyl.

Examples of preferred compounds of formula I, wherein R¹, R², R³ and R⁴are defined individually in the tables A1 to A154, and R⁵ and R⁶ or R⁹and R¹⁰ are defined individually in the table A.

-   Table A1: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is H, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A2: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is H, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A3: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is H, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A4: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is H, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A5: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is H, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A6: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is H, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A7: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is H, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A8: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is H, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A9: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is H, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A10: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is H, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A11: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is H, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A12: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is F, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A13: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is F, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A14: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is F, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A15: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is F, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A16: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is F, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A17: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is F, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A18: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is F, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A19: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is F, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A20: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is F, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A21: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is F, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A22: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is F, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A23: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Cl, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A24: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Cl, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A25: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Cl, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A26: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Cl, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A27: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Cl, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A28: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Cl, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A29: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Cl, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A30: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Cl, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A31: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Cl, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A32: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Cl, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A33: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Cl, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A34: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Br, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A35: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Br, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A36: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Br, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A37: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Br, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A38: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Br, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A39: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Br, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A40: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Br, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A41: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Br, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A42: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Br, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A43: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Br, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A44: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is Br, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A45: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is J, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A46: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is J, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A47: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is J, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A48: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is J, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A49: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is J, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A50: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is J, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A51: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is J, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A52: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is J, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A53: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is J, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A54: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is J, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A55: Compounds of formula I, wherein each of R³ and R⁴ are H,    R² is J, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A56: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is F, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A57: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is F, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A58: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is F, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A59: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is F, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A60: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is F, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A61: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is F, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A62: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is F, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A63: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is F, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A64: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is F, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A65: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is F, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A66: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is F, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A67: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Cl, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A68: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Cl, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A69: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Cl, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A70: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Cl, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A71: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Cl, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A72: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Cl, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A73: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Cl, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A74: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Cl, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A75: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Cl, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A76: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Cl, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A77: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Cl, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A78: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Br, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A79: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Br, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A80: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Br, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A81: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Br, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A82: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Br, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A83: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Br, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A84: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Br, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A85: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Br, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A86: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Br, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A87: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Br, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A88: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is Br, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A89: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A90: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A91: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A92: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A93: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A94: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A95: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A96: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A97: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A98: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A99: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A100: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is F, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A101: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is F, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A102: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A103: Compounds of formula I, wherein each of R² and R⁴ are H,    R³ is J, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A104: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is F, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A105: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is F, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A106: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is F, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A107: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is F, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A108: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is F, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A109: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is F, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A110: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is F, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A111: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Cl, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A112: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Cl, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A113: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Cl, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A114: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Cl, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A115: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Cl, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A116: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Cl, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A117: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Cl, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A118: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Cl, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A119: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Cl, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A120: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Cl, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A121: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Cl, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A122: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Br, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A123: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Br, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A124: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Br, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A125: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Br, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A126: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Br, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A127: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Br, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A128: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Br, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A129: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Br, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A130: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Br, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A131: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Br, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A132: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is Br, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A133: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is J, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A134: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is J, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A135: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is J, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A136: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is J, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A137: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is J, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A138: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is J, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A139: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is J, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A140: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is J, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A141: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is J, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A142: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is J, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A143: Compounds of formula I, wherein each of R³ and R² are H,    R⁴ is J, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A144: Compounds of formula I, wherein each of R⁴ and R² are F,    R³ is H, R¹ is CH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A145: Compounds of formula I, wherein each of R⁴ and R² are F,    R³ is H, R¹ is C₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A146: Compounds of formula I, wherein each of R⁴ and R² are F,    R³ is H, R¹ is Cl and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A147: Compounds of formula I, wherein each of R⁴ and R² are F,    R³ is H, R¹ is F and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as defined    in one row of table A;-   Table A148: Compounds of formula I, wherein each of R⁴ and R² are F,    R³ is H, R¹ is CF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A149: Compounds of formula I, wherein each of R⁴ and R² are F,    R³ is H, R¹ is OCH₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A150: Compounds of formula I, wherein each of R⁴ and R² are F,    R³ is H, R¹ is OC₂H₅ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A151: Compounds of formula I, wherein each of R⁴ and R² are F,    R³ is H, R¹ is OCF₃ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A152: Compounds of formula I, wherein each of R⁴ and R² are F,    R³ is H, R¹ is OCHF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A153: Compounds of formula I, wherein each of R⁴ and R² are F,    R³ is H, R¹ is OCClF₂ and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;-   Table A154: Compounds of formula I, wherein each of R⁴ and R² are F,    R³ is H, R¹ is OCF₂CHClF and wherein R⁵ and R⁶ or R⁹ and R¹⁰ are as    defined in one row of table A;

TABLE A R⁵, R⁶, resp. resp. N° Formula R⁹ R¹⁰ C.I-1

CH₃ CH₃ C.I-2 I.A¹.2 CH₃ CH₃CH₂ C.I-3 I.A¹.2 CH₃ CH₃CH₂CH₂ C.I-4 I.A¹.2CH₃ (CH₃)₂CH C.I-5 I.A¹.2 CH₃ F₃C C.I-6 I.A¹.2 CH₃CH₂ CH₃CH₂ C.I-7I.A¹.2 CH₃CH₂ CH₃CH₂CH₂ C.I-8 I.A¹.2 CH₃CH₂ (CH₃)₂CH C.I-9 I.A¹.2 CH₃CH₂F₃C C.I-10 I.A¹.2 CH₃CH₂CH₂ CH₃CH₂CH₂ C.I-11 I.A¹.2 CH₃CH₂CH₂ (CH₃)₂CHC.I-12 I.A¹.2 CH₃CH₂CH₂ F₃C C.I-13 I.A¹.2 (CH₃)₂CH (CH₃)₂CH C.I-14I.A¹.2 (CH₃)₂CH F₃C C.I-15 I.A¹.2 F₃C F₃C C.I-16 I.A¹.2—CH₂—CH₂—CH₂—CH₂— C.I-17 I.A¹.2 —CH₂—CH₂—CH₂—CH₂—CH₂— C.I-18 I.A¹.2—CH₂—S—CH₂—CH₂— C.I-19

CH₃ CH₃ C.I-20 I.A¹.1 CH₃ CH₃CH₂ C.I-21 I.A¹.1 CH₃ CH₃CH₂CH₂ C.I-22I.A¹.1 CH₃ (CH₃)₂CH C.I-23 I.A¹.1 CH₃ F₃C C.I-24 I.A¹.1 CH₃CH₂ CH₃CH₂C.I-25 I.A¹.1 CH₃CH₂ CH₃CH₂CH₂ C.I-26 I.A¹.1 CH₃CH₂ (CH₃)₂CH C.I-27I.A¹.1 CH₃CH₂ F₃C C.I-28 I.A¹.1 CH₃CH₂CH₂ CH₃CH₂CH₂ C.I-29 I.A¹.1CH₃CH₂CH₂ (CH₃)₂CH C.I-30 I.A¹.1 CH₃CH₂CH₂ F₃C C.I-31 I.A¹.1 (CH₃)₂CH(CH₃)₂CH C.I-32 I.A¹.1 (CH₃)₂CH F₃C C.I-33 I.A¹.1 F₃C F₃C C.I-34 I.A¹.1—CH₂—CH₂—CH₂—CH₂— C.I-35 I.A¹.1 —CH₂—CH₂—CH₂—CH₂—CH₂— C.I-36 I.A¹.1—CH₂—S—CH₂—CH₂— C.I-37

CH₃ CH₃ C.I-38 I.A¹.0 CH₃ CH₃CH₂ C.I-39 I.A¹.0 CH₃ CH₃CH₂CH₂ C.I-40I.A¹.0 CH₃ (CH₃)₂CH C.I-41 I.A¹.0 CH₃ F₃C C.I-42 I.A¹.0 CH₃CH₂ CH₃CH₂C.I-43 I.A¹.0 CH₃CH₂ CH₃CH₂CH₂ C.I-44 I.A¹.0 CH₃CH₂ (CH₃)₂CH C.I-45I.A¹.0 CH₃CH₂ F₃C C.I-46 I.A¹.0 CH₃CH₂CH₂ CH₃CH₂CH₂ C.I-47 I.A¹.0CH₃CH₂CH₂ (CH₃)₂CH C.I-48 I.A¹.0 CH₃CH₂CH₂ F₃C C.I-49 I.A¹.0 (CH₃)₂CH(CH₃)₂CH C.I-50 I.A¹.0 (CH₃)₂CH F₃C C.I-51 I.A¹.0 F₃C F₃C C.I-52 I.A¹.0—CH₂—CH₂—CH₂—CH₂— C.I-53 I.A¹.0 —CH₂—CH₂—CH₂—CH₂—CH₂— C.I-54 I.A¹.0—CH₂—S—CH₂—CH₂— C.I-55

CH₃ H C.I-56 I.A³.0 CH₃ F₃C C.I-57 I.A³.0 CH₃ Cl₃C C.I-58 I.A³.0 CH₃Cl₂CH C.I-59 I.A³.0 CH₃ ClCH₂ C.I-60 I.A³.0 CH₃ CH₃ C.I-61 I.A³.0 CH₃CH₃CH₂ C.I-62 I.A³.0 CH₃ (CH₃)₂CH C.I-63 I.A³.0 CH₃ (CH₃)₃C C.I-64I.A³.0 CH₃ CH₃CH₂CH₂ C.I-65 I.A³.0 CH₃ CH₃CH₂CH₂CH₂ C.I-66 I.A³.0 CH₃(CH₃)₃CCH₂ C.I-67 I.A³.0 CH₃ CH₃O C.I-68 I.A³.0 CH₃ CH₃CH₂O C.I-69I.A³.0 CH₃ F₃CCH₂O C.I-70 I.A³.0 CH₃ CH₃NH C.I-71 I.A³.0 CH₃ CH₃CH₂NHC.I-72 I.A³.0 CH₃ (CH₃)₂N C.I-73 I.A³.0 CH₃ (CH₃CH₂)₂N C.I-74 I.A³.0 CH₃(CH₃CH₂)CH₃N C.I-75 I.A³.0 CH₃ C₆H₅ NH C.I-76 I.A³.0 CH₃ (C₆H₅)CH₃NC.I-77 I.A³.0 CH₃ (2,6-F₂C₆H₃) NH C.I-78 I.A³.0 CH₃ (2,6-F₂C₆H₃)CH₃NC.I-79 I.A³.0 CH₃ cyclopropyl C.I-80 I.A³.0 CH₃ cyclobutyl C.I-81 I.A³.0CH₃ cyclopentyl C.I-82 I.A³.0 CH₃ cyclohexyl C.I-83 I.A³.0 CH₃ CNCH₂C.I-84 I.A³.0 CH₃ CH₃OCH₂ C.I-85 I.A³.0 CH₃ CH₃CH₂OCH₂ C.I-86 I.A³.0 CH₃CH₃OCH₂CH₂ C.I-87 I.A³.0 CH₃ F₃C CH₂ C.I-88 I.A³.0 CH₃ CH₃OCOCH₂ C.I-89I.A³.0 CH₃ CH₃SCH₂ C.I-90 I.A³.0 CH₃ CH₃CH₂SCH₂ C.I-91 I.A³.0 CH₃CH₃SCH₂CH₂ C.I-92 I.A³.0 CH₃ C₆H₅CH₂ C.I-93 I.A³.0 CH₃ CH₂═CHCH₂ C.I-94I.A³.0 CH₃ CH₂═CH C.I-95 I.A³.0 CH₃ CH₃CH═CH C.I-96 I.A³.0 CH₃ C₆H₅C.I-97 I.A³.0 CH₃ 2-F—C₆H₄ C.I-98 I.A³.0 CH₃ 3-F—C₆H₄ C.I-99 I.A³.0 CH₃4-F—C₆H₄ C.I-100 I.A³.0 CH₃ 2-Cl—C₆H₄ C.I-101 I.A³.0 CH₃ 3-Cl—C₆H₄C.I-102 I.A³.0 CH₃ 4-Cl—C₆H₄ C.I-103 I.A³.0 CH₃ 2-CH₃—C₆H₄ C.I-104I.A³.0 CH₃ 3-CH₃—C₆H₄ C.I-105 I.A³.0 CH₃ 4-CH₃—C₆H₄ C.I-106 I.A³.0 CH₃2-CH₃O—C₆H₄ C.I-107 I.A³.0 CH₃ 3-CH₃O—C₆H₄ C.I-108 I.A³.0 CH₃4-CH₃O—C₆H₄ C.I-109 I.A³.0 CH₃ 2-F₃O—C₆H₄ C.I-110 I.A³.0 CH₃ 3-F₃O—C₆H₄C.I-111 I.A³.0 CH₃ 4-F₃O—C₆H₄ C.I-112 I.A³.0 CH₃ 2-Br—C₆H₄ C.I-113I.A³.0 CH₃ 3-Br—C₆H₄ C.I-114 I.A³.0 CH₃ 4-Br—C₆H₄ C.I-115 I.A³.0 CH₃3-CN—C₆H₄ C.I-116 I.A³.0 CH₃ 4-CN—C₆H₄ C.I-117 I.A³.0 CH₃ pyridin-2-ylC.I-118 I.A³.0 CH₃ pyridin-3-yl C.I-119 I.A³.0 CH₃ pyridin-4-yl C.I-120I.A³.0 CH₃ 2-methyl-pyridin-5-yl C.I-121 I.A³.0 CH₃3-methyl-pyridin-2-yl C.I-122 I.A³.0 CH₃ 2-chloro-pyridin-3-yl C.I-123I.A³.0 CH₃ 2-chloro-pyridin-4-yl C.I-124 I.A³.0 CH₃2-chloro-pyridin-5-yl C.I-125 I.A³.0 CH₃ 2-chloro-pyridin-6-yl C.I-126I.A³.0 CH₃ 2-chloro-pyridin-6-yl C.I-127 I.A³.0 CH₃ 4-trifluoromethyl-pyridin-3-yl C.I-128 I.A³.0 CH₃ 3-methylthio- pyridin-3-yl C.I-129I.A³.0 CH₃ 2,3-dichloro-pyridin- 5-yl C.I-130 I.A³.0 CH₃2,5-dichloro-pyridin- 3-yl C.I-131 I.A³.0 CH₃ 2,6-dichloro-pyridin- 3-ylC.I-132 I.A³.0 CH₃ 3,5-dichloro-pyridin- 4-yl C.I-133 I.A³.0 CH₃N-methyl-pyrrol-2-yl C.I-134 I.A³.0 CH₃ pyrazin-2-yl C.I-135 I.A³.0 CH₃4-trifluoromethyl- pyrimidin-5-yl C.I-136 I.A³.0 CH₃ furan-2-yl C.I-137I.A³.0 CH₃ furan-3-yl C.I-138 I.A³.0 CH₃ 2-tetrahydrofuranyl C.I-139I.A³.0 CH₃ 3-tetrahydrofuranyl C.I-140 I.A³.0 CH₃ thiophen-2-yl C.I-141I.A³.0 CH₃ thiophen-3-yl C.I-142 I.A³.0 CH₃ 1-methyl-3-trifluoro-methyl-1H-pyrazol- 4-yl C.I-143 I.A³.0 CH₃ 1-methyl-5-trifluoro-methyl-1H-pyrazol- 4-yl C.I-144 I.A³.0 CH₃ isoxazol-5-yl C.I-145 I.A³.0CH₃ 2,4-dimethyl- thiazol-5-yl C.I-146 I.A³.0 CH₃ 4-trifluoromethyl-thiazol-5-yl C.I-147 I.A³.0 CH₃ 3-methyl-isothiazol- 5-yl C.I-148 I.A³.0CH₃ 3,4-dichloro- isothiazol-5-yl C.I-149 I.A³.0 CH₃CH₂ H C.I-150 I.A³.0CH₃CH₂ F₃C C.I-151 I.A³.0 CH₃CH₂ Cl₃C C.I-152 I.A³.0 CH₃CH₂ Cl₂CHC.I-153 I.A³.0 CH₃CH₂ ClCH₂ C.I-154 I.A³.0 CH₃CH₂ CH₃ C.I-155 I.A³.0CH₃CH₂ CH₃CH₂ C.I-156 I.A³.0 CH₃CH₂ (CH₃)₂CH C.I-157 I.A³.0 CH₃CH₂(CH₃)₃C C.I-158 I.A³.0 CH₃CH₂ CH₃CH₂CH₂ C.I-159 I.A³.0 CH₃CH₂CH₃CH₂CH₂CH₂ C.I-160 I.A³.0 CH₃CH₂ (CH₃)₃CCH₂ C.I-161 I.A³.0 CH₃CH₂ CH₃OC.I-162 I.A³.0 CH₃CH₂ CH₃CH₂O C.I-163 I.A³.0 CH₃CH₂ F₃CCH₂O C.I-164I.A³.0 CH₃CH₂ CH₃NH C.I-165 I.A³.0 CH₃CH₂ CH₃CH₂NH C.I-166 I.A³.0 CH₃CH₂(CH₃)₂N C.I-167 I.A³.0 CH₃CH₂ (CH₃CH₂)₂N C.I-168 I.A³.0 CH₃CH₂(CH₃CH₂)CH₃N C.I-169 I.A³.0 CH₃CH₂ C₆H₅ NH C.I-170 I.A³.0 CH₃CH₂(C₆H₅)CH₃N C.I-171 I.A³.0 CH₃CH₂ (2,6-F₂C₆H₃) NH C.I-172 I.A³.0 CH₃CH₂(2,6-F₂C₆H₃)CH₃N C.I-173 I.A³.0 CH₃CH₂ cyclopropyl C.I-174 I.A³.0 CH₃CH₂cyclobutyl C.I-175 I.A³.0 CH₃CH₂ cyclopentyl C.I-176 I.A³.0 CH₃CH₂cyclohexyl C.I-177 I.A³.0 CH₃CH₂ CNCH₂ C.I-178 I.A³.0 CH₃CH₂ CH₃OCH₂C.I-179 I.A³.0 CH₃CH₂ CH₃CH₂OCH₂ C.I-180 I.A³.0 CH₃CH₂ CH₃OCH₂CH₂C.I-181 I.A³.0 CH₃CH₂ F₃C CH₂ C.I-182 I.A³.0 CH₃CH₂ CH₃OCOCH₂ C.I-183I.A³.0 CH₃CH₂ CH₃SCH₂ C.I-184 I.A³.0 CH₃CH₂ CH₃CH₂SCH₂ C.I-185 I.A³.0CH₃CH₂ CH₃SCH₂CH₂ C.I-186 I.A³.0 CH₃CH₂ C₆H₅CH₂ C.I-187 I.A³.0 CH₃CH₂CH₂═CHCH₂ C.I-188 I.A³.0 CH₃CH₂ CH₂═CH C.I-189 I.A³.0 CH₃CH₂ CH₃CH═CHC.I-190 I.A³.0 CH₃CH₂ C₆H₅ C.I-191 I.A³.0 CH₃CH₂ 2-F—C₆H₄ C.I-192 I.A³.0CH₃CH₂ 3-F—C₆H₄ C.I-193 I.A³.0 CH₃CH₂ 4-F—C₆H₄ C.I-194 I.A³.0 CH₃CH₂2-Cl—C₆H₄ C.I-195 I.A³.0 CH₃CH₂ 3-Cl—C₆H₄ C.I-196 I.A³.0 CH₃CH₂4-Cl—C₆H₄ C.I-197 I.A³.0 CH₃CH₂ 2-CH₃—C₆H₄ C.I-198 I.A³.0 CH₃CH₂3-CH₃—C₆H₄ C.I-199 I.A³.0 CH₃CH₂ 4-CH₃—C₆H₄ C.I-200 I.A³.0 CH₃CH₂2-CH₃O—C₆H₄ C.I-201 I.A³.0 CH₃CH₂ 3-CH₃O—C₆H₄ C.I-202 I.A³.0 CH₃CH₂4-CH₃O—C₆H₄ C.I-203 I.A³.0 CH₃CH₂ 2-F₃C—C₆H₄ C.I-204 I.A³.0 CH₃CH₂3-F₃C—C₆H₄ C.I-205 I.A³.0 CH₃CH₂ 4-F₃C—C₆H₄ C.I-206 I.A³.0 CH₃CH₂2-Br—C₆H₄ C.I-207 I.A³.0 CH₃CH₂ 3-Br—C₆H₄ C.I-208 I.A³.0 CH₃CH₂4-Br—C₆H₄ C.I-209 I.A³.0 CH₃CH₂ 3-CN—C₆H₄ C.I-210 I.A³.0 CH₃CH₂4-CN—C₆H₄ C.I-211 I.A³.0 CH₃CH₂ pyridin-2-yl C.I-212 I.A³.0 CH₃CH₂pyridin-3-yl C.I-213 I.A³.0 CH₃CH₂ pyridin-4-yl C.I-214 I.A³.0 CH₃CH₂2-methyl-pyridin-5-yl C.I-215 I.A³.0 CH₃CH₂ 3-methyl-pyridin-2-ylC.I-216 I.A³.0 CH₃CH₂ 2-chloro-pyridin-3-yl C.I-217 I.A³.0 CH₃CH₂2-chloro-pyridin-4-yl C.I-218 I.A³.0 CH₃CH₂ 2-chloro-pyridin-5-ylC.I-219 I.A³.0 CH₃CH₂ 2-chloro-pyridin-6-yl C.I-220 I.A³.0 CH₃CH₂2-chloro-pyridin-6-yl C.I-221 I.A³.0 CH₃CH₂ 4-trifluoromethyl-pyridin-3-yl C.I-222 I.A³.0 CH₃CH₂ 3-methylthio- pyridin-3-yl C.I-223I.A³.0 CH₃CH₂ 2,3-dichloro-pyridin- 5-yl C.I-224 I.A³.0 CH₃CH₂2,5-dichloro-pyridin- 3-yl C.I-225 I.A³.0 CH₃CH₂ 2,6-dichloro-pyridin-3-yl C.I-226 I.A³.0 CH₃CH₂ 3,5-dichloro-pyridin- 4-yl C.I-227 I.A³.0CH₃CH₂ N-methypyrrol-2-yl C.I-228 I.A³.0 CH₃CH₂ pyrazin-2-yl C.I-229I.A³.0 CH₃CH₂ 4-trifluoromethyl- pyrimidin-5-yl C.I-230 I.A³.0 CH₃CH₂furan-2-yl C.I-231 I.A³.0 CH₃CH₂ furan-3-yl C.I-232 I.A³.0 CH₃CH₂2-tetrahydrofuranyl C.I-233 I.A³.0 CH₃CH₂ 3-tetrahydrofuranyl C.I-234I.A³.0 CH₃CH₂ thiophen-2-yl C.I-235 I.A³.0 CH₃CH₂ thiophen-3-yl C.I-236I.A³.0 CH₃CH₂ 1-methyl-3-trifluoro- methyl-1H-pyrazol- 4-yl C.I-237I.A³.0 CH₃CH₂ 1-methyl-5-trifluoro- methyl-1H-pyrazol- 4-yl C.I-238I.A³.0 CH₃CH₂ isoxazol-5-yl C.I-239 I.A³.0 CH₃CH₂ 2,4-dimethyl-thiazol-5-yl C.I-240 I.A³.0 CH₃CH₂ 4-trifluoromethyl- thiazol-5-ylC.I-241 I.A³.0 CH₃CH₂ 3-methyl-isothiazol- 5-yl C.I-242 I.A³.0 CH₃CH₂3,4-dichloro- isothiazol-5-yl C.I-243 I.A³.0 CH₃CH₂CH₂ H C.I-244 I.A³.0CH₃CH₂CH₂ F₃C C.I-245 I.A³.0 CH₃CH₂CH₂ Cl₃C C.I-246 I.A³.0 CH₃CH₂CH₂Cl₂CH C.I-247 I.A³.0 CH₃CH₂CH₂ ClCH₂ C.I-248 I.A³.0 CH₃CH₂CH₂ CH₃C.I-249 I.A³.0 CH₃CH₂CH₂ CH₃CH₂ C.I-250 I.A³.0 CH₃CH₂CH₂ (CH₃)₂CHC.I-251 I.A³.0 CH₃CH₂CH₂ (CH₃)₃C C.I-252 I.A³.0 CH₃CH₂CH₂ CH₃CH₂CH₂C.I-253 I.A³.0 CH₃CH₂CH₂ CH₃CH₂CH₂CH₂ C.I-254 I.A³.0 CH₃CH₂CH₂(CH₃)₃CCH₂ C.I-255 I.A³.0 CH₃CH₂CH₂ CH₃O C.I-256 I.A³.0 CH₃CH₂CH₂CH₃CH₂O C.I-257 I.A³.0 CH₃CH₂CH₂ F₃CCH₂O C.I-258 I.A³.0 CH₃CH₂CH₂ CH₃NHC.I-259 I.A³.0 CH₃CH₂CH₂ CH₃CH₂NH C.I-260 I.A³.0 CH₃CH₂CH₂ (CH₃)₂NC.I-261 I.A³.0 CH₃CH₂CH₂ (CH₃CH₂)₂N C.I-262 I.A³.0 CH₃CH₂CH₂(CH₃CH₂)CH₃N C.I-263 I.A³.0 CH₃CH₂CH₂ C₆H₅ NH C.I-264 I.A³.0 CH₃CH₂CH₂(C₆H₅)CH₃N C.I-265 I.A³.0 CH₃CH₂CH₂ (2,6-F₂C₆H₃) NH C.I-266 I.A³.0CH₃CH₂CH₂ (2,6-F₂C₆H₃)CH₃N C.I-267 I.A³.0 CH₃CH₂CH₂ cyclopropyl C.I-268I.A³.0 CH₃CH₂CH₂ cyclobutyl C.I-269 I.A³.0 CH₃CH₂CH₂ cyclopentyl C.I-270I.A³.0 CH₃CH₂CH₂ cyclohexyl C.I-271 I.A³.0 CH₃CH₂CH₂ CNCH₂ C.I-272I.A³.0 CH₃CH₂CH₂ CH₃OCH₂ C.I-273 I.A³.0 CH₃CH₂CH₂ CH₃CH₂OCH₂ C.I-274I.A³.0 CH₃CH₂CH₂ CH₃OCH₂CH₂ C.I-275 I.A³.0 CH₃CH₂CH₂ F₃C CH₂ C.I-276I.A³.0 CH₃CH₂CH₂ CH₃OCOCH₂ C.I-277 I.A³.0 CH₃CH₂CH₂ CH₃SCH₂ C.I-278I.A³.0 CH₃CH₂CH₂ CH₃CH₂SCH₂ C.I-279 I.A³.0 CH₃CH₂CH₂ CH₃SCH₂CH₂ C.I-280I.A³.0 CH₃CH₂CH₂ C₆H₅CH₂ C.I-281 I.A³.0 CH₃CH₂CH₂ CH₂═CHCH₂ C.I-282I.A³.0 CH₃CH₂CH₂ CH₂═CH C.I-283 I.A³.0 CH₃CH₂CH₂ CH₃CH═CH C.I-284 I.A³.0CH₃CH₂CH₂ C₆H₅ C.I-285 I.A³.0 CH₃CH₂CH₂ 2-F—C₆H₄ C.I-286 I.A³.0CH₃CH₂CH₂ 3-F—C₆H₄ C.I-287 I.A³.0 CH₃CH₂CH₂ 4-F—C₆H₄ C.I-288 I.A³.0CH₃CH₂CH₂ 2-Cl—C₆H₄ C.I-289 I.A³.0 CH₃CH₂CH₂ 3-Cl—C₆H₄ C.I-290 I.A³.0CH₃CH₂CH₂ 4-Cl—C₆H₄ C.I-291 I.A³.0 CH₃CH₂CH₂ 2-CH₃—C₆H₄ C.I-292 I.A³.0CH₃CH₂CH₂ 3-CH₃—C₆H₄ C.I-293 I.A³.0 CH₃CH₂CH₂ 4-CH₃—C₆H₄ C.I-294 I.A³.0CH₃CH₂CH₂ 2-CH₃O—C₆H₄ C.I-295 I.A³.0 CH₃CH₂CH₂ 3-CH₃O—C₆H₄ C.I-296I.A³.0 CH₃CH₂CH₂ 4-CH₃O—C₆H₄ C.I-297 I.A³.0 CH₃CH₂CH₂ 2-F₃C—C₆H₄ C.I-298I.A³.0 CH₃CH₂CH₂ 3-F₃C—C₆H₄ C.I-299 I.A³.0 CH₃CH₂CH₂ 4-F₃C—C₆H₄ C.I-300I.A³.0 CH₃CH₂CH₂ 2-Br—C₆H₄ C.I-301 I.A³.0 CH₃CH₂CH₂ 3-Br—C₆H₄ C.I-302I.A³.0 CH₃CH₂CH₂ 4-Br—C₆H₄ C.I-303 I.A³.0 CH₃CH₂CH₂ 3-CN—C₆H₄ C.I-304I.A³.0 CH₃CH₂CH₂ 4-CN—C₆H₄ C.I-305 I.A³.0 CH₃CH₂CH₂ pyridin-2-yl C.I-306I.A³.0 CH₃CH₂CH₂ pyridin-3-yl C.I-307 I.A³.0 CH₃CH₂CH₂ pyridin-4-ylC.I-308 I.A³.0 CH₃CH₂CH₂ 2-methyl-pyridin-5-yl C.I-309 I.A³.0 CH₃CH₂CH₂3-methyl-pyridin-2-yl C.I-310 I.A³.0 CH₃CH₂CH₂ 2-chloro-pyridin-3-ylC.I-311 I.A³.0 CH₃CH₂CH₂ 2-chloro-pyridin-4-yl C.I-312 I.A³.0 CH₃CH₂CH₂2-chloro-pyridin-5-yl C.I-313 I.A³.0 CH₃CH₂CH₂ 2-chloro-pyridin-6-ylC.I-314 I.A³.0 CH₃CH₂CH₂ 2-chloro-pyridin-6-yl C.I-315 I.A³.0 CH₃CH₂CH₂4-trifluoromethyl- pyridin-3-yl C.I-316 I.A³.0 CH₃CH₂CH₂ 3-methylthio-pyridin-3-yl C.I-317 I.A³.0 CH₃CH₂CH₂ 2,3-dichloro-pyridin- 5-yl C.I-318I.A³.0 CH₃CH₂CH₂ 2,5-dichloro-pyridin- 3-yl C.I-319 I.A³.0 CH₃CH₂CH₂2,6-dichloro-pyridin- 3-yl C.I-320 I.A³.0 CH₃CH₂CH₂3,5-dichloro-pyridin- 4-yl C.I-321 I.A³.0 CH₃CH₂CH₂ N-methy-pyrrol-2-ylC.I-322 I.A³.0 CH₃CH₂CH₂ pyrazin-2-yl C.I-323 I.A³.0 CH₃CH₂CH₂4-trifluoromethyl- pyrimidin-5-yl C.I-324 I.A³.0 CH₃CH₂CH₂ furan-2-ylC.I-325 I.A³.0 CH₃CH₂CH₂ furan-3-yl C.I-326 I.A³.0 CH₃CH₂CH₂2-tetrahydrofuranyl C.I-327 I.A³.0 CH₃CH₂CH₂ 3-tetrahydrofuranyl C.I-328I.A³.0 CH₃CH₂CH₂ thiophen-2-yl C.I-329 I.A³.0 CH₃CH₂CH₂ thiophen-3-ylC.I-330 I.A³.0 CH₃CH₂CH₂ 1-methyl-3-trifluoro- methyl-1H-pyrazol- 4-ylC.I-331 I.A³.0 CH₃CH₂CH₂ 1-methyl-5-trifluoro- methyl-1H-pyrazol- 4-ylC.I-332 I.A³.0 CH₃CH₂CH₂ isoxazol-5-yl C.I-333 I.A³.0 CH₃CH₂CH₂2,4-dimethyl- thiazol-5-yl C.I-334 I.A³.0 CH₃CH₂CH₂ 4-trifluoromethyl-thiazol-5-yl C.I-335 I.A³.0 CH₃CH₂CH₂ 3-methyl-isothiazol- 5-yl C.I-336I.A³.0 CH₃CH₂CH₂ 3,4-dichloro- isothiazol-5-yl C.I-337

CH₃ H C.I-338 I.A³.1 CH₃ F₃C C.I-339 I.A³.1 CH₃ Cl₃C C.I-340 I.A³.1 CH₃Cl₂CH C.I-341 I.A³.1 CH₃ ClCH₂ C.I-342 I.A³.1 CH₃ CH₃ C.I-343 I.A³.1 CH₃CH₃CH₂ C.I-344 I.A³.1 CH₃ (CH₃)₂CH C.I-345 I.A³.1 CH₃ (CH₃)₃C C.I-346I.A³.1 CH₃ CH₃CH₂CH₂ C.I-347 I.A³.1 CH₃ CH₃CH₂CH₂CH₂ C.I-348 I.A³.1 CH₃(CH₃)₃CCH₂ C.I-349 I.A³.1 CH₃ CH₃O C.I-350 I.A³.1 CH₃ CH₃CH₂O C.I-351I.A³.1 CH₃ F₃CCH₂O C.I-352 I.A³.1 CH₃ CH₃NH C.I-353 I.A³.1 CH₃ CH₃CH₂NHC.I-354 I.A³.1 CH₃ (CH₃)₂N C.I-355 I.A³.1 CH₃ (CH₃CH₂)₂N C.I-356 I.A³.1CH₃ (CH₃CH₂)CH₃N C.I-357 I.A³.1 CH₃ C₆H₅ NH C.I-358 I.A³.1 CH₃(C₆H₅)CH₃N C.I-359 I.A³.1 CH₃ (2,6-F₂C₆H₃) NH C.I-360 I.A³.1 CH₃(2,6-F₂C₆H₃)CH₃N C.I-361 I.A³.1 CH₃ cyclopropyl C.I-362 I.A³.1 CH₃cyclobutyl C.I-363 I.A³.1 CH₃ cyclopentyl C.I-364 I.A³.1 CH₃ cyclohexylC.I-365 I.A³.1 CH₃ CNCH₂ C.I-366 I.A³.1 CH₃ CH₃OCH₂ C.I-367 I.A³.1 CH₃CH₃CH₂OCH₂ C.I-368 I.A³.1 CH₃ CH₃OCH₂CH₂ C.I-369 I.A³.1 CH₃ F₃C CH₂C.I-370 I.A³.1 CH₃ CH₃OCOCH₂ C.I-371 I.A³.1 CH₃ CH₃SCH₂ C.I-372 I.A³.1CH₃ CH₃CH₂SCH₂ C.I-373 I.A³.1 CH₃ CH₃SCH₂CH₂ C.I-374 I.A³.1 CH₃ C₆H₅CH₂C.I-375 I.A³.1 CH₃ CH₂═CHCH₂ C.I-376 I.A³.1 CH₃ CH₂═CH C.I-377 I.A³.1CH₃ CH₃CH═CH C.I-378 I.A³.1 CH₃ C₆H₅ C.I-379 I.A³.1 CH₃ 2-F—C₆H₄ C.I-380I.A³.1 CH₃ 3-F—C₆H₄ C.I-381 I.A³.1 CH₃ 4-F—C₆H₄ C.I-382 I.A³.1 CH₃2-Cl—C₆H₄ C.I-383 I.A³.1 CH₃ 3-Cl—C₆H₄ C.I-384 I.A³.1 CH₃ 4-Cl—C₆H₄C.I-385 I.A³.1 CH₃ 2-CH₃—C₆H₄ C.I-386 I.A³.1 CH₃ 3-CH₃—C₆H₄ C.I-387I.A³.1 CH₃ 4-CH₃—C₆H₄ C.I-388 I.A³.1 CH₃ 2-CH₃O—C₆H₄ C.I-389 I.A³.1 CH₃3-CH₃O—C₆H₄ C.I-390 I.A³.1 CH₃ 4-CH₃O—C₆H₄ C.I-391 I.A³.1 CH₃ 2-F₃C—C₆H₄C.I-392 I.A³.1 CH₃ 3-F₃C—C₆H₄ C.I-393 I.A³.1 CH₃ 4-F₃C—C₆H₄ C.I-394I.A³.1 CH₃ 2-Br—C₆H₄ C.I-395 I.A³.1 CH₃ 3-Br—C₆H₄ C.I-396 I.A³.1 CH₃4-Br—C₆H₄ C.I-397 I.A³.1 CH₃ 3-CN—C₆H₄ C.I-398 I.A³.1 CH₃ 4-CN—C₆H₄C.I-399 I.A³.1 CH₃ pyridin-2-yl C.I-400 I.A³.1 CH₃ pyridin-3-yl C.I-401I.A³.1 CH₃ pyridin-4-yl C.I-402 I.A³.1 CH₃ 2-methyl-pyridin-5-yl C.I-403I.A³.1 CH₃ 3-methyl-pyridin-2-yl C.I-404 I.A³.1 CH₃2-chloro-pyridin-3-yl C.I-405 I.A³.1 CH₃ 2-chloro-pyridin-4-yl C.I-406I.A³.1 CH₃ 2-chloro-pyridin-5-yl C.I-407 I.A³.1 CH₃2-chloro-pyridin-6-yl C.I-408 I.A³.1 CH₃ 2-chloro-pyridin-6-yl C.I-409I.A³.1 CH₃ 4-trifluoromethyl- pyridin-3-yl C.I-410 I.A³.1 CH₃3-methylthio- pyridin-3-yl C.I-411 I.A³.1 CH₃ 2,3-dichloro-pyridin- 5-ylC.I-412 I.A³.1 CH₃ 2,5-dichloro-pyridin- 3-yl C.I-413 I.A³.1 CH₃2,6-dichloro-pyridin- 3-yl C.I-414 I.A³.1 CH₃ 3,5-dichloro-pyridin- 4-ylC.I-415 I.A³.1 CH₃ N-methyl-pyrrol-2-yl C.I-416 I.A³.1 CH₃ pyrazin-2-ylC.I-417 I.A³.1 CH₃ 4-trifluoromethyl- pyrimidin-5-yl C.I-418 I.A³.1 CH₃furan-2-yl C.I-419 I.A³.1 CH₃ furan-3-yl C.I-420 I.A³.1 CH₃2-tetrahydrofuranyl C.I-421 I.A³.1 CH₃ 3-tetrahydrofuranyl C.I-422I.A³.1 CH₃ thiophen-2-yl C.I-423 I.A³.1 CH₃ thiophen-3-yl C.I-424 I.A³.1CH₃ 1 -methyl-3-trifluoro- methyl-1H-pyrazol- 4-yl C.I-425 I.A³.1 CH₃ 1-methyl-5-trifluoro- methyl-1H-pyrazol- 4-yl C.I-426 I.A³.1 CH₃isoxazol-5-yl C.I-427 I.A³.1 CH₃ 2,4-dimethyl- thiazol-5-yl C.I-428I.A³.1 CH₃ 4-trifluoromethyl- thiazol-5-yl C.I-429 I.A³.1 CH₃3-methyl-isothiazol- 5-yl C.I-430 I.A³.1 CH₃ 3,4-dichloro-isothiazol-5-yl C.I-431 I.A³.1 CH₃CH₂ H C.I-432 I.A³.1 CH₃CH₂ F₃CC.I-433 I.A³.1 CH₃CH₂ Cl₃C C.I-434 I.A³.1 CH₃CH₂ Cl₂CH C.I-435 I.A³.1CH₃CH₂ ClCH₂ C.I-436 I.A³.1 CH₃CH₂ CH₃ C.I-437 I.A³.1 CH₃CH₂ CH₃CH₂C.I-438 I.A³.1 CH₃CH₂ (CH₃)₂CH C.I-439 I.A³.1 CH₃CH₂ (CH₃)₃C C.I-440I.A³.1 CH₃CH₂ CH₃CH₂CH₂ C.I-441 I.A³.1 CH₃CH₂ CH₃CH₂CH₂CH₂ C.I-442I.A³.1 CH₃CH₂ (CH₃)₃CCH₂ C.I-443 I.A³.1 CH₃CH₂ CH₃O C.I-444 I.A³.1CH₃CH₂ CH₃CH₂O C.I-445 I.A³.1 CH₃CH₂ F₃CCH₂O C.I-446 I.A³.1 CH₃CH₂ CH₃NHC.I-447 I.A³.1 CH₃CH₂ CH₃CH₂NH C.I-448 I.A³.1 CH₃CH₂ (CH₃)₂N C.I-449I.A³.1 CH₃CH₂ (CH₃CH₂)₂N C.I-450 I.A³.1 CH₃CH₂ (CH₃CH₂)CH₃N C.I-451I.A³.1 CH₃CH₂ C₆H₅ NH C.I-452 I.A³.1 CH₃CH₂ (C₆H₅)CH₃N C.I-453 I.A³.1CH₃CH₂ (2,6-F₂C₆H₃) NH C.I-454 I.A³.1 CH₃CH₂ (2,6-F₂C₆H₃)CH₃N C.I-455I.A³.1 CH₃CH₂ cyclopropyl C.I-456 I.A³.1 CH₃CH₂ cyclobutyl C.I-457I.A³.1 CH₃CH₂ cyclopentyl C.I-458 I.A³.1 CH₃CH₂ cyclohexyl C.I-459I.A³.1 CH₃CH₂ CNCH₂ C.I-460 I.A³.1 CH₃CH₂ CH₃OCH₂ C.I-461 I.A³.1 CH₃CH₂CH₃CH₂OCH₂ C.I-462 I.A³.1 CH₃CH₂ CH₃OCH₂CH₂ C.I-463 I.A³.1 CH₃CH₂ F₃CCH₂ C.I-464 I.A³.1 CH₃CH₂ CH₃OCOCH₂ C.I-465 I.A³.1 CH₃CH₂ CH₃SCH₂C.I-466 I.A³.1 CH₃CH₂ CH₃CH₂SCH₂ C.I-467 I.A³.1 CH₃CH₂ CH₃SCH₂CH₂C.I-468 I.A³.1 CH₃CH₂ C₆H₅CH₂ C.I-469 I.A³.1 CH₃CH₂ CH₂═CHCH₂ C.I-470I.A³.1 CH₃CH₂ CH₂═CH C.I-471 I.A³.1 CH₃CH₂ CH₃CH═CH C.I-472 I.A³.1CH₃CH₂ C₆H₅ C.I-473 I.A³.1 CH₃CH₂ 2-F—C₆H₄ C.I-474 I.A³.1 CH₃CH₂3-F—C₆H₄ C.I-475 I.A³.1 CH₃CH₂ 4-F—C₆H₄ C.I-476 I.A³.1 CH₃CH₂ 2-Cl—C₆H₄C.I-477 I.A³.1 CH₃CH₂ 3-Cl—C₆H₄ C.I-478 I.A³.1 CH₃CH₂ 4-Cl—C₆H₄ C.I-479I.A³.1 CH₃CH₂ 2-CH₃—C₆H₄ C.I-480 I.A³.1 CH₃CH₂ 3-CH₃—C₆H₄ C.I-481 I.A³.1CH₃CH₂ 4-CH₃—C₆H₄ C.I-482 I.A³.1 CH₃CH₂ 2-CH₃O—C₆H₄ C.I-483 I.A³.1CH₃CH₂ 3-CH₃O—C₆H₄ C.I-484 I.A³.1 CH₃CH₂ 4-CH₃O—C₆H₄ C.I-485 I.A³.1CH₃CH₂ 2-F₃C—C₆H₄ C.I-486 I.A³.1 CH₃CH₂ 3-F₃C—C₆H₄ C.I-487 I.A³.1 CH₃CH₂4-F₃C—C₆H₄ C.I-488 I.A³.1 CH₃CH₂ 2-Br—C₆H₄ C.I-489 I.A³.1 CH₃CH₂3-Br—C₆H₄ C.I-490 I.A³.1 CH₃CH₂ 4-Br—C₆H₄ C.I-491 I.A³.1 CH₃CH₂3-CN—C₆H₄ C.I-492 I.A³.1 CH₃CH₂ 4-CN—C₆H₄ C.I-493 I.A³.1 CH₃CH₂pyridin-2-yl C.I-494 I.A³.1 CH₃CH₂ pyridin-3-yl C.I-495 I.A³.1 CH₃CH₂pyridin-4-yl C.I-496 I.A³.1 CH₃CH₂ 2-methyl-pyridin-5-yl C.I-497 I.A³.1CH₃CH₂ 3-methyl-pyridin-2-yl C.I-498 I.A³.1 CH₃CH₂ 2-chloro-pyridin-3-ylC.I-499 I.A³.1 CH₃CH₂ 2-chloro-pyridin-4-yl C.I-500 I.A³.1 CH₃CH₂2-chloro-pyridin-5-yl C.I-501 I.A³.1 CH₃CH₂ 2-chloro-pyridin-6-ylC.I-502 I.A³.1 CH₃CH₂ 2-chloro-pyridin-6-yl C.I-503 I.A³.1 CH₃CH₂4-trifluoromethyl- pyridin-3-yl C.I-504 I.A³.1 CH₃CH₂ 3-methylthio-pyridin-3-yl C.I-505 I.A³.1 CH₃CH₂ 2,3-dichloro-pyridin- 5-yl C.I-506I.A³.1 CH₃CH₂ 2,5-dichloro-pyridin- 3-yl C.I-507 I.A³.1 CH₃CH₂2,6-dichloro-pyridin- 3-yl C.I-508 I.A³.1 CH₃CH₂ 3,5-dichloro-pyridin-4-yl C.I-509 I.A³.1 CH₃CH₂ N-methypyrrol-2-yl C.I-510 I.A³.1 CH₃CH₂pyrazin-2-yl C.I-511 I.A³.1 CH₃CH₂ 4-trifluoromethyl- pyrimidin-5-ylC.I-512 I.A³.1 CH₃CH₂ furan-2-yl C.I-513 I.A³.1 CH₃CH₂ furan-3-ylC.I-514 I.A³.1 CH₃CH₂ 2-tetrahydrofuranyl C.I-515 I.A³.1 CH₃CH₂3-tetrahydrofuranyl C.I-516 I.A³.1 CH₃CH₂ thiophen-2-yl C.I-517 I.A³.1CH₃CH₂ thiophen-3-yl C.I-518 I.A³.1 CH₃CH₂ 1-methyl-3-trifluoro-methyl-1H-pyrazol- 4-yl C.I-519 I.A³.1 CH₃CH₂ 1-methyl-5-trifluoro-methyl-1H-pyrazol- 4-yl C.I-520 I.A³.1 CH₃CH₂ isoxazol-5-yl C.I-521I.A³.1 CH₃CH₂ 2,4-dimethyl- thiazol-5-yl C.I-522 I.A³.1 CH₃CH₂4-trifluoromethyl- thiazol-5-yl C.I-523 I.A³.1 CH₃CH₂3-methyl-isothiazol- 5-yl C.I-524 I.A³.1 CH₃CH₂ 3,4-dichloro-isothiazol-5-yl C.I-525

CH₃ H C.I-526 I.A³.2 CH₃ F₃C C.I-527 I.A³.2 CH₃ Cl₃C C.I-528 I.A³.2 CH₃Cl₂CH C.I-529 I.A³.2 CH₃ ClCH₂ C.I-530 I.A³.2 CH₃ CH₃ C.I-531 I.A³.2 CH₃CH₃CH₂ C.I-532 I.A³.2 CH₃ (CH₃)₂CH C.I-533 I.A³.2 CH₃ (CH₃)₃C C.I-534I.A³.2 CH₃ CH₃CH₂CH₂ C.I-535 I.A³.2 CH₃ CH₃CH₂CH₂CH₂ C.I-536 I.A³.2 CH₃(CH₃)₃CCH₂ C.I-537 I.A³.2 CH₃ CH₃O C.I-538 I.A³.2 CH₃ CH₃CH₂O C.I-539I.A³.2 CH₃ F₃CCH₂O C.I-540 I.A³.2 CH₃ CH₃NH C.I-541 I.A³.2 CH₃ CH₃CH₂NHC.I-542 I.A³.2 CH₃ (CH₃)₂N C.I-543 I.A³.2 CH₃ (CH₃CH₂)₂N C.I-544 I.A³.2CH₃ (CH₃CH₂)CH₃N C.I-545 I.A³.2 CH₃ C₆H₅ NH C.I-546 I.A³.2 CH₃(C₆H₅)CH₃N C.I-547 I.A³.2 CH₃ (2,6-F₂C₆H₃) NH C.I-548 I.A³.2 CH₃(2,6-F₂C₆H₃)CH₃N C.I-549 I.A³.2 CH₃ cyclopropyl C.I-550 I.A³.2 CH₃cyclobutyl C.I-551 I.A³.2 CH₃ cyclopentyl C.I-552 I.A³.2 CH₃ cyclohexylC.I-553 I.A³.2 CH₃ CNCH₂ C.I-554 I.A³.2 CH₃ CH₃OCH₂ C.I-555 I.A³.2 CH₃CH₃CH₂OCH₂ C.I-556 I.A³.2 CH₃ CH₃OCH₂CH₂ C.I-557 I.A³.2 CH₃ F₃C CH₂C.I-558 I.A³.2 CH₃ CH₃OCOCH₂ C.I-559 I.A³.2 CH₃ CH₃SCH₂ C.I-560 I.A³.2CH₃ CH₃CH₂SCH₂ C.I-561 I.A³.2 CH₃ CH₃SCH₂CH₂ C.I-562 I.A³.2 CH₃ C₆H₅CH₂C.I-563 I.A³.2 CH₃ CH₂═CHCH₂ C.I-564 I.A³.2 CH₃ CH₂═CH C.I-565 I.A³.2CH₃ CH₃CH═CH C.I-566 I.A³.2 CH₃ C₆H₅ C.I-567 I.A³.2 CH₃ 2-F—C₆H₄ C.I-568I.A³.2 CH₃ 3-F—C₆H₄ C.I-569 I.A³.2 CH₃ 4-F—C₆H₄ C.I-570 I.A³.2 CH₃2-Cl—C₆H₄ C.I-571 I.A³.2 CH₃ 3-Cl—C₆H₄ C.I-572 I.A³.2 CH₃ 4-Cl—C₆H₄C.I-573 I.A³.2 CH₃ 2-CH₃—C₆H₄ C.I-574 I.A³.2 CH₃ 3-CH₃—C₆H₄ C.I-575I.A³.2 CH₃ 4-CH₃—C₆H₄ C.I-576 I.A³.2 CH₃ 2-CH₃O—C₆H₄ C.I-577 I.A³.2 CH₃3-CH₃O—C₆H₄ C.I-578 I.A³.2 CH₃ 4-CH₃O—C₆H₄ C.I-579 I.A³.2 CH₃ 2-F₃C—C₆H₄C.I-580 I.A³.2 CH₃ 3-F₃C—C₆H₄ C.I-581 I.A³.2 CH₃ 4-F₃C—C₆H₄ C.I-582I.A³.2 CH₃ 2-Br—C₆H₄ C.I-583 I.A³.2 CH₃ 3-Br—C₆H₄ C.I-584 I.A³.2 CH₃4-Br—C₆H₄ C.I-585 I.A³.2 CH₃ 3-CN—C₆H₄ C.I-586 I.A³.2 CH₃ 4-CN—C₆H₄C.I-587 I.A³.2 CH₃ pyridin-2-yl C.I-588 I.A³.2 CH₃ pyridin-3-yl C.I-589I.A³.2 CH₃ pyridin-4-yl C.I-590 I.A³.2 CH₃ 2-methyl-pyridin-5-yl C.I-591I.A³.2 CH₃ 3-methyl-pyridin-2-yl C.I-592 I.A³.2 CH₃2-chloro-pyridin-3-yl C.I-593 I.A³.2 CH₃ 2-chloro-pyridin-4-yl C.I-594I.A³.2 CH₃ 2-chloro-pyridin-5-yl C.I-595 I.A³.2 CH₃2-chloro-pyridin-6-yl C.I-596 I.A³.2 CH₃ 2-chloro-pyridin-6-yl C.I-597I.A³.2 CH₃ 4-trifluoromethyl- pyridin-3-yl C.I-598 I.A³.2 CH₃3-methylthio- pyridin-3-yl C.I-599 I.A³.2 CH₃ 2,3-dichloro-pyridin- 5-ylC.I-600 I.A³.2 CH₃ 2,5-dichloro-pyridin- 3-yl C.I-601 I.A³.2 CH₃2,6-dichloro-pyridin- 3-yl C.I-602 I.A³.2 CH₃ 3,5-dichloro-pyridin- 4-ylC.I-603 I.A³.2 CH₃ N-methyl-pyrrol-2-yl C.I-604 I.A³.2 CH₃ pyrazin-2-ylC.I-605 I.A³.2 CH₃ 4-trifluoromethyl- pyrimidin-5-yl C.I-606 I.A³.2 CH₃furan-2-yl C.I-607 I.A³.2 CH₃ furan-3-yl C.I-608 I.A³.2 CH₃2-tetrahydrofuranyl C.I-609 I.A³.2 CH₃ 3-tetrahydrofuranyl C.I-610I.A³.2 CH₃ thiophen-2-yl C.I-611 I.A³.2 CH₃ thiophen-3-yl C.I-612 I.A³.2CH₃ 1-methyl-3-trifluoro- methyl-1H-pyrazol- 4-yl C.I-613 I.A³.2 CH₃1-methyl-5-trifluoro- methyl-1H-pyrazol- 4-yl C.I-614 I.A³.2 CH₃isoxazol-5-yl C.I-615 I.A³.2 CH₃ 2,4-dimethyl- thiazol-5-yl C.I-616I.A³.2 CH₃ 4-trifluoromethyl- thiazol-5-yl C.I-617 I.A³.2 CH₃3-methyl-isothiazol- 5-yl C.I-618 I.A³.2 CH₃ 3,4-dichloro-isothiazol-5-yl C.I-619 I.A³.2 CH₃CH₂ H C.I-620 I.A³.2 CH₃CH₂ F₃CC.I-621 I.A³.2 CH₃CH₂ Cl₃C C.I-622 I.A³.2 CH₃CH₂ Cl₂CH C.I-623 I.A³.2CH₃CH₂ ClCH₂ C.I-624 I.A³.2 CH₃CH₂ CH₃ C.I-625 I.A³.2 CH₃CH₂ CH₃CH₂C.I-626 I.A³.2 CH₃CH₂ (CH₃)₂CH C.I-627 I.A³.2 CH₃CH₂ (CH₃)₃C C.I-628I.A³.2 CH₃CH₂ CH₃CH₂CH₂ C.I-629 I.A³.2 CH₃CH₂ CH₃CH₂CH₂CH₂ C.I-630I.A³.2 CH₃CH₂ (CH₃)₃CCH₂ C.I-631 I.A³.2 CH₃CH₂ CH₃O C.I-632 I.A³.2CH₃CH₂ CH₃CH₂O C.I-633 I.A³.2 CH₃CH₂ F₃CCH₂O C.I-634 I.A³.2 CH₃CH₂ CH₃NHC.I-635 I.A³.2 CH₃CH₂ CH₃CH₂NH C.I-636 I.A³.2 CH₃CH₂ (CH₃)₂N C.I-637I.A³.2 CH₃CH₂ (CH₃CH₂)₂N C.I-638 I.A³.2 CH₃CH₂ (CH₃CH₂)CH₃N C.I-639I.A³.2 CH₃CH₂ C₆H₅ NH C.I-640 I.A³.2 CH₃CH₂ (C₆H₅)CH₃N C.I-641 I.A³.2CH₃CH₂ (2,6-F₂C₆H₃) NH C.I-642 I.A³.2 CH₃CH₂ (2,6-F₂C₆H₃)CH₃N C.I-643I.A³.2 CH₃CH₂ cyclopropyl C.I-644 I.A³.2 CH₃CH₂ cyclobutyl C.I-645I.A³.2 CH₃CH₂ cyclopentyl C.I-646 I.A³.2 CH₃CH₂ cyclohexyl C.I-647I.A³.2 CH₃CH₂ CNCH₂ C.I-648 I.A³.2 CH₃CH₂ CH₃OCH₂ C.I-649 I.A³.2 CH₃CH₂CH₃CH₂OCH₂ C.I-650 I.A³.2 CH₃CH₂ CH₃OCH₂CH₂ C.I-651 I.A³.2 CH₃CH₂ F₃CCH₂ C.I-652 I.A³.2 CH₃CH₂ CH₃OCOCH₂ C.I-653 I.A³.2 CH₃CH₂ CH₃SCH₂C.I-654 I.A³.2 CH₃CH₂ CH₃CH₂SCH₂ C.I-655 I.A³.2 CH₃CH₂ CH₃SCH₂CH₂C.I-656 I.A³.2 CH₃CH₂ C₆H₅CH₂ C.I-657 I.A³.2 CH₃CH₂ CH₂═CHCH₂ C.I-658I.A³.2 CH₃CH₂ CH₂═CH C.I-659 I.A³.2 CH₃CH₂ CH₃CH═CH C.I-660 I.A³.2CH₃CH₂ C₆H5 C.I-661 I.A³.2 CH₃CH₂ 2-F—C₆H₄ C.I-662 I.A³.2 CH₃CH₂3-F—C₆H₄ C.I-663 I.A³.2 CH₃CH₂ 4-F—C₆H₄ C.I-664 I.A³.2 CH₃CH₂ 2-Cl—C₆H₄C.I-665 I.A³.2 CH₃CH₂ 3-Cl—C₆H₄ C.I-666 I.A³.2 CH₃CH₂ 4-Cl—C₆H₄ C.I-667I.A³.2 CH₃CH₂ 2-CH₃—C₆H₄ C.I-668 I.A³.2 CH₃CH₂ 3-CH₃—C₆H₄ C.I-669 I.A³.2CH₃CH₂ 4-CH₃—C₆H₄ C.I-670 I.A³.2 CH₃CH₂ 2-CH₃O—C₆H₄ C.I-671 I.A³.2CH₃CH₂ 3-CH₃O—C₆H₄ C.I-672 I.A³.2 CH₃CH₂ 4-CH₃O—C₆H₄ C.I-673 I.A³.2CH₃CH₂ 2-F₃C—C₆H₄ C.I-674 I.A³.2 CH₃CH₂ 3-F₃C—C₆H₄ C.I-675 I.A³.2 CH₃CH₂4-F₃C—C₆H₄ C.I-676 I.A³.2 CH₃CH₂ 2-Br—C₆H₄ C.I-677 I.A³.2 CH₃CH₂3-Br—C₆H₄ C.I-678 I.A³.2 CH₃CH₂ 4-Br—C₆H₄ C.I-679 I.A³.2 CH₃CH₂3-CN—C₆H₄ C.I-680 I.A³.2 CH₃CH₂ 4-CN—C₆H₄ C.I-681 I.A³.2 CH₃CH₂pyridin-2-yl C.I-682 I.A³.2 CH₃CH₂ pyridin-3-yl C.I-683 I.A³.2 CH₃CH₂pyridin-4-yl C.I-684 I.A³.2 CH₃CH₂ 2-methyl-pyridin-5-yl C.I-685 I.A³.2CH₃CH₂ 3-methyl-pyridin-2-yl C.I-686 I.A³.2 CH₃CH₂ 2-chloro-pyridin-3-ylC.I-687 I.A³.2 CH₃CH₂ 2-chloro-pyridin-4-yl C.I-688 I.A³.2 CH₃CH₂2-chloro-pyridin-5-yl C.I-689 I.A³.2 CH₃CH₂ 2-chloro-pyridin-6-ylC.I-690 I.A³.2 CH₃CH₂ 2-chloro-pyridin-6-yl C.I-691 I.A³.2 CH₃CH₂4-trifluoromethyl- pyridin-3-yl C.I-692 I.A³.2 CH₃CH₂ 3-methylthio-pyridin-3-yl C.I-693 I.A³.2 CH₃CH₂ 2,3-dichloro-pyridin- 5-yl C.I-694I.A³.2 CH₃CH₂ 2,5-dichloro-pyridin- 3-yl C.I-695 I.A³.2 CH₃CH₂2,6-dichloro-pyridin- 3-yl C.I-696 I.A³.2 CH₃CH₂ 3,5-dichloro-pyridin-4-yl C.I-697 I.A³.2 CH₃CH₂ N-methypyrrol-2-yl C.I-698 I.A³.2 CH₃CH₂pyrazin-2-yl C.I-699 I.A³.2 CH₃CH₂ 4-trifluoromethyl- pyrimidin-5-ylC.I-700 I.A³.2 CH₃CH₂ furan-2-yl C.I-701 I.A³.2 CH₃CH₂ furan-3-ylC.I-702 I.A³.2 CH₃CH₂ 2-tetrahydrofuranyl C.I-703 I.A³.2 CH₃CH₂3-tetrahydrofuranyl C.I-704 I.A³.2 CH₃CH₂ thiophen-2-yl C.I-705 I.A³.2CH₃CH₂ thiophen-3-yl C.I-706 I.A³.2 CH₃CH₂ 1-methyl-3-trifluoro-methyl-1H-pyrazol- 4-yl C.I-707 I.A³.2 CH₃CH₂ 1-methyl-5-trifluoro-methyl-1H-pyrazol- 4-yl C.I-708 I.A³.2 CH₃CH₂ isoxazol-5-yl C.I-709I.A³.2 CH₃CH₂ 2,4-dimethyl- thiazol-5-yl C.I-710 I.A³.2 CH₃CH₂4-trifluoromethyl- thiazol-5-yl C.I-711 I.A³.2 CH₃CH₂3-methyl-isothiazol- 5-yl C.I-712 I.A³.2 CH₃CH₂ 3,4-dichloro-isothiazol-5-ylPreparation MethodsCompounds of the Formula I

wherein A has the meaning

and the other substituents and variables are as defined above forformula I, can be prepared in general by reacting an activatedbenzisothiazolone of formula II-a:

wherein Y is halogen or O—SO₂R and R is therein an alkyl, haloalkyl or asubstituted phenyl (e.g. Y is mesylate, triflate andpara-toluenesulfonate), and wherein R¹, R², R³ and R⁴ are as defined forformula I.

In case of A is A¹ or A² e.g. in presence of a base with a compound ofthe formula A¹-H or A²-H,

wherein the variables R⁵, R⁶, R⁷ and R⁸ are analgously as defined asbefore for formula I.

Suitable activated derivatives of the benzisothiazolone-derivative offormula II-a which may be used are, for example the3-halobenzisothiazole-derivatives as 3-Chloro-benzisothiazole or asmentioned above the corresponding sulfonates, e.g. the triflates ormesylates.

The activated derivatives of the benzisothiazolone of formula II-a canbe obtained according to the following schemes:

P.0. 3-Amino-benzisothiazole

3-Amino-benzisothiazoles (P0-I) can be prepared by heating a suitablysubstituted disulfide (P0-II) together with an amine and an oxidizingagent such as dimethylsulfoxide (DMSO) in a polar solvent such asisopropanol as described by S. W. Walinsky et al. in Organic ProcessResearch & Development 1999, 3, 126-130.

The 2-cyano-disulfides (P0-II) can be prepared from the correspondingthiophenols (P0-III) by using oxidizing agents such as dimethylsulfoxid(DMSO) as reported by H. Boerzel et al. in Inorganic Chemistry 2003,1604-1615.

2-cyano-thiophenols (P0-III) can be prepared from benzisothiazoles(P0-IV) by treatment with strong bases such as NaOCH₃ as described by J.Markert et al. in Liebigs Annalen d. Chemie 1980, 768-778.

Said article also describes the synthesis of substitutedbenzisothiazoles (P0-IV) from 2-chloro-benzaldahydes (P0-V) via reactionwith sulfur and ammonia.

Alternatively, the 2-cyano-disulfides (P0-II) can be prepared from2-cyano-anilines (P0-VI) via diazotation and subsequent reaction of thediazonium-salt with Na₂S and sulfur as described by V. M. Negrimovsky etal. in Phosphorus, Sulfur & The Related Elements 1995, 104, 161-167.

2-cyano-anilines (P0-VI) can be prepared from 2-cyano-nitrobenzenes(P0-VII) with a reducing agent such as iron as described by D. H.Klaubert in J. Med. Chem. 1981, 24, 742-748.

Alternatively 3-amino-1,2-benzisothiazoles (P0-I) can be prepared from3-chloro-benzo[d]isothiazole (P0-VIIIa) as described by H. Boeshagen etal. in Justus Liebig Annalen der Chemie, 1977, 20.

The Chloro-benzo[d]isothiazoles (P0-VIIIa) can be obtained frombenzisothiazolones (P0-IX) by reaction with a chlorinating agent such asPCl₃ (described by J. P. Yevich et al. in Journal of Medicinal Chemistry1986, 29, 359-369) or PCl₃/PCl₅ (S. G. Zlutin et al. Journal of OrganicChemistry 2000, 65, 8439-8443).

3-amino-1,2-benzisothiazoles (P0-I) can also be obtained fromtrifluoromethanesulfonic acid benzo[d]isothiazol-3-yl ester (P0-VIIIb)in analogy to U.S. Pat. No. 5,359,068 by reaction of said compounds withamines. This latter reference describes the trifluoro-methanesulfonicacid benzo[d]isothiazol-3-yl ester (P0-VIIIb) obtained frombenzisothiazolones.

The above mentioned reference of S. G. Zlutin et al. also describes thesynthesis of said benzisothiazolones (P0-IX) from2-benzylsulfanyl-benzamides (P0-X) via treatment with an oxidizing agentsuch as SO₂Cl₂.

Alternatively, another method for preparing benzisothiazolones (P-XIV)from 2-(alkythio)benzonitriles (P-XVI) in a one-pot procedure isdescribed in EP 1081141.

P.1 Aminobenzisothiazole-1-mono-oxides

Aminobenzisothiazole (P0-I) can be oxidized in analogy to a proceduredescribed in Chemische Berichte, 103, 3166-3181 to yield themono-oxygenated species (P1-I). Suitable oxidizing reagents are e.g.HNO₃, H₂O₂/acetic acid or m-chlor-perbenzoic acid.

P.2 3-Aminobenzisothiazole-1,1-dioxides

3-Aminobenzisothiazole-1,1-dioxides (P2-I) can be obtained from suitablysubstituted 3-Chloro-benzo[d]isothiazole 1,1-dioxides (P2-II) byreaction with a primary amine in a polar, non-protic solvent such astetrahydrofurane or dioxane as described in Journal of the ChemicalSociety Perkin Transaction 2, 2001, 1315-1324.

3-Chloro-benzo[d]isothiazole 1,1-dioxides (P2-II) can be prepared by thereaction of a suitably substituted saccharine (P2-III) with achlorinating agent such as ClCO₂CCl₃, PCl₅/POCl₃ or SOCl₂ as describedby D. Dopp et al. in Synthesis 2001, 8, 1228-1235, by R. Salman in Chem.Eng. Data 1987, 32, 391 or by R. W. Lang in Helvetica Chimica Acta 1989,72, 1248-1252.

Substituted saccharines (P2-III) can be prepared via reaction of2-chlorosulfonyl-benzoic acid esters (P2-IV) with ammonia as it isdescribed by M. C. Bell et al. in Bioorganic & Medicinal Letters 1991,No. 12, 733-736 or M. L. Trudell et al. in Journal of Heterocyclic Chem.2004, 41, 435f.

The latter article also describes the synthesis of mentioned2-chlorosulfonyl-benzoic acid esters (P2-IV) from the correspondingmethyl anthranilates (P2-V) via diazotation and subsequentchlorosulfonation. A similar synthetic procedure is described by G.Hamprecht et al. in Chimia (2004), 58, 117-122.

In cases where the methyl anthranilates (P2-V) are not commerciallyavailable, they can be prepared from the corresponding 2-nitro benzoicacid methyl ester (P2-VI) via catalytic hydrogenation as mentioned by J.F. W. Keana et al. in Bioorganic & Medicinal Chemistry 11 (2003)1769-1780.

Alternatively, saccharines (P2-II) can be prepared by cleavage of thecorresponding N-t-butyl saccharines (P2-VII) via heating with a strongacid such as trifluoroacetic acid in a way described by K. F. Burri inHelvetica Chimica Acta 1990, 73, 69-80.

N-t-butyl saccharines (P2-VII) can be obtained from the correspondingsulfonamides (P2-VIII) by directed ortho metallation with bases such asbutyllithium or lithiumdiiso-propylamide and subsequent trapping of themetallated species with carbon dioxide under ring-closure. The procedureis described by D. Becker et al. in Tetrahedron 1992, 2515-2522. Themetallation can be carried out as described by N. Murugesan et al. in J.Med. Chem. 1998, 41, 5198-5218.

Alternatively, 3-amino-1,2-benzisothiazole 1,1-dioxides (P2-I) can alsobe prepared from suitably substituted imidates (P2-IX) via a reactionwith primary amines at elevated temperature. The reaction can be carriedout either neat or in a suitable solvent, preferentially a polar,high-boiling solvent such as tetrahydrofuran (THF) or dioxane.Preferentially, the reaction is carried out neat. In cases were thereaction is carried out neat, the preferred temperature is between roomtemperature and the boiling point of the respective amine. In cases werethe reaction is carried out in a solvent, the preferred temperature isbetween room temperature and the boiling point of the respectivesolvent. The substituent Alkyl in this method is preferentially analkyl-substituent such as methyl or ethyl.

Said imidates (P2-IX) can be obtained by reacting a 2-cyanobenzenesulfonamide (P2-X) with a carbonic acid orthoester in a processsimilarly described in Journal of Organic Chemistry 1963, 28, 2902-2903.Said cyanobenzene sulfonamides (P2-X) can be prepared as described in WO2005/035486.

Compounds I-A1-0 of the present invention for which A has the meaningdefined as A¹ and m=0 can be made via a condensation reaction ofaminobenzisothiazole-derivative III-a with suitably substitutedsulfoxides IV in combination with a suitable condensating agent.Suitable condensing agents are, for example, phosphorous oxychloride,phosphorous (V) oxide, methanesulfonyl chloride, sulfuryl chloride,sulfur trichloride, boron trifluoride, dicyclohexylcarbodiimide, arylcyanates or acid anhydrides, preferably trifluoroacetic anhydride ortrifluoromethanesulfonic anhydride.

Sulfoxides of formula IV can be obtained according to procedures knownin the art, e.g. as described in J. March, Advanced Organic Chemistry,4th Edition, Wiley, 1992, p. 1297.

Alternatively, said compounds can be prepared by reacting a suitablysubstituted activated benzisothiazolone II-a with suitably substitutedthio-compound V in presence of a base. Preferentially this base is anamine such as triethylamine or N-diisopropyletylamine (Huenig's base).

Thio-compounds V can be prepared following a procedure described inTetrahedron 1975, 31, 3035-3040.

In cases, where n is 0, 1 or 2, compounds I-A1-1 for which m=1, can beobtained from compounds I-A1-0 for which m=0 by treatment with anappropriate oxidizing agent such as H₂O₂, NaOCl or 3-chloro-perbenzoeicacid in analogy to syntheses described in Journal of HeterocyclicChemistry 2005, 42, 599-607 (H₂O₂), Journal of Organic Chemistry 1984,49, 2282-2284 (NaOCl) or Heterocycles 1998, 49, 181-190(meta-chloro-perbenzoic acid (mcpba)):

Compounds I-A2 in which A has the meaning given for A² can be obtainedfrom ami-nobenzisothiazole-derivatives III-b via reaction with suitablysubstituted thio-compounds VI in the presence of a base in analogy tosyntheses described in Farmaco 1992, 47, 265-274. Suitable bases wouldbe, for example, amines such as triethylamine, Huenig's base orpyridine.

3-amino-1,2-benzisothiazoles (P0-I) can also be obtained from2-mercapto-benzonitriles (P0-XII) or their alkali metal salts in analogyto L. K. A. Rahman et al., J. Chem. Soc. Perkin Trans I, 1983, 2973-2977by reaction of said compounds with amines.

Compounds I-A3 in which A has the meaning given for A³ can be obtainedfrom aminobenzisothiazole-derivatives via reaction with an acyl halide(Hal-C(O)—R¹⁰), especially an acyl chloride, an acid anhydride(R¹⁰—C(O)—O—C(O)—R¹⁰) or a mixed acid anhydride in the presence of anappropriate base according to procedures known in the art, e.g. EP133418. Appropriate bases include organic bases, for example tertiaryamines, such as aliphatic amines, for example trimethylamine,triethylamine or diisopropylethylamine, cycloaliphatic tertiary amines,for example N-methylpiperidine, or aromatic amines, for examplepyridine, substituted pyridines such as 2,4,6-collidine, 2,4-lutidine or4-dimethylaminopyridine.

In the preparation methods described above, the variables R¹, R², R³,R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰ have the meanings as defined above, inparticular the meanings mentioned as being preferred.

If individual compounds cannot be prepared via the above-describedroutes, they can be prepared by derivatization of other compounds I orby customary modifications of the synthesis routes described.

The reaction mixtures are worked up in the customary manner, for exampleby mixing with water, separating the phases, and, if appropriate,purifying the crude products by chromatography, for example on aluminaor silica gel. Some of the intermediates and end products may beobtained in the form of colorless or pale brown viscous oils, which arefreed or purified from volatile components under reduced pressure and atmoderately elevated temperature. If the intermediates and end productsare obtained as solids, they may be purified by recrystallization ordigestion.

Agriculturally acceptable salts of the compounds of formula I can beformed in a customary manner, e.g. by reaction with an acid of the anionin question.

Pests

The compounds of the formula I are especially suitable for efficientlycombating the following pests:

-   insects from the order of the lepidopterans (Lepidoptera), for    example Agrotis ypsilon, Agrotis segetum, Alabama argillacea,    Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma,    Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia    brumata, Choristoneura fumiferana, Choristoneura occidentalis,    Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania    nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus    lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia    subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha    molesta, Heliothis armigera, Heliothis virescens, Heliothis zea,    Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta    malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma    exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis    blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria    dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria,    Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis,    Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera    bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris    brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia    includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga    cerealella, Sparganothis pilleriana, Spodoptera frugiperda,    Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa,    Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis,-   beetles (Coleoptera), for example Agrilus sinuatus, Agriotes    lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus    dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae,    Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda,    Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus    lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata,    Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi,    Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi,    Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata,    Diabrotica 12-punctata Diabrotica speciosa, Diabrotica virgifera,    Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus    brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera    postica, Ips typographus, Lema bilineata, Lema melanopus,    Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus    oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha    hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus    sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius    pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha    horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia    japonica, Sitona lineatus and Sitophilus granaria,-   flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus,    Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles    crucians, Anopheles albimanus, Anopheles gambiae, Anopheles    freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles    quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya    bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops    discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia    hominivorax, Contarinia sorghicola Cordylobia anthropophaga,    Culicoides furens, Culex pipiens, Culex nigripalpus, Culex    quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta    melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia    antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia    hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus    intestinalis, Glossina morsitans, Glossina palpalis, Glossina    fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis    equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata,    Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia    caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis,    Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca    domestica, Muscina stabulans, Oestrus ovis, Opomyza florum,    Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia    brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora    columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum,    Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis,    Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus    bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis,    Tipula oleracea, and Tipula paludosa-   thrips (Thysanoptera), e.g. Dichromothrips corbetti, Dichromothrips    ssp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella    tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips    tabaci,-   termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes    flavipes, Heterotermes aureus, Reticulitermes flavipes,    Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes    santonensis, Reticulitermes grassei, Termes natalensis, and    Coptotermes formosanus,-   cockroaches (Blattaria-Blattodea), e.g. Blattella germanica,    Blattella asahinae, Periplaneta americana, Periplaneta japonica,    Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta    australasiae, and Blatta orientalis,-   bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas    (Hemiptera), e.g. Acrosternum hilare, Blissus leucopterus,    Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius,    Eurygaster integriceps, Euschistus impictiventris, Leptoglossus    phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula,    Piesma quadrata, Solubea insularis, Thyanta perditor, Acyrthosiphon    onobrychis, Adelges laricis, Aphidula nasturtii, tii, Aphis fabae,    Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis    schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum,    Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui,    Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus    prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha    gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia    nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum    pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae,    Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae,    Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae,    Melanaphis pyrarius, Metopolophium dirhodum, Myzus persicae, Myzus    ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri,    Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida,    Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus,    Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum,    Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura    lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera    aurantiiand, Viteus vitifolii, Cimex lectularius, Cimex hemipterus,    Reduvius senilis, Triatoma spp., and Arilus critatus.-   ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Atta    cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta    robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa    minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis,    Solenopsis geminata, Solenopsis invicta, Solenopsis richteri,    Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus,    Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula    squamosa, Paravespula vulgaris, Paravespula pennsylvanica,    Paravespula germanica, Dolichovespula maculata, Vespa crabro,    Polistes rubiginosa, Camponotus floridanus, and Linepithema humile,-   crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica,    Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus,    Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus    sanguinipes, Melanoplus spretus, Nomadacris septemfasciata,    Schistocerca americana, Schistocerca gregaria, Dociostaurus    maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus    variegatus, Hieroglyphus daganensis, Kraussaria angulifera,    Calliptamus italicus, Chortoicetes terminifera, and Locustana    pardalina,-   Arachnoidea, such as arachnids (Acarina), e.g. of the families    Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum,    Amblyomma variegatum, Ambryomma maculatum, Argas persicus, Boophilus    annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor    silvarum, Dermacentor andersoni, Dermacentor variabilis, Hyalomma    truncatum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis,    Ixodes holocyclus, Ixodes pacificus, Ornithodorus moubata,    Ornithodorus hermsi, Ornithodorus turicata, Ornithonyssus bacoti,    Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus    sanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi,    Sarcoptes scabiei, and Eriophyidae spp. such as Aculus    schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni;    Tarsonemidae spp. such as Phytonemus pallidus and    Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus    phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus,    Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius    and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and    Oligonychus pratensis; Araneida, e.g. Latrodectus mactans, and    Loxosceles reclusa,-   fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides    canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and    Nosopsyllus fasciatus,-   silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and    Thermobia domestica,-   centipedes (Chilopoda), e.g. Scutigera coleoptrata,-   millipedes (Diplopoda), e.g. Narceus spp.,-   earwigs (Dermaptera), e.g. forficula auricularia,-   lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus    humanus corporis, Pthirus pubis, Haematopinus eurysternus,    Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon    gallinae, Menacanthus stramineus and Solenopotes capillatus.-   springtails (Collembola), e.g. Onychiurus ssp.

They are also suitable for controlling Nematodes: plant parasiticnematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyneincognita, Meloidogyne javanica, and other Meloidogyne species;cyst-forming nematodes, Globodera rostochiensis and other Globoderaspecies; Heterodera avenae, Heterodera glycines, Heterodera schachtii,Heterodera trifolii, and other Heterodera species; Seed gall nematodes,Anguina species; Stem and foliar nematodes, Aphelenchoides species;Sting nematodes, Belonolaimus longicaudatus and other Belonolaimusspecies; Pine nematodes, Bursaphelenchus xylophilus and otherBursaphelenchus species; Ring nematodes, Criconema species, Criconemellaspecies, Criconemoides species, Mesocriconema species; Stem and bulbnematodes, Ditylenchus destructor, Ditylenchus dipsaci and otherDitylenchus species; Awl nematodes, Dolichodorus species; Spiralnematodes, Heliocotylenchus multicinctus and other Helicotylenchusspecies; Sheath and sheathoid nematodes, Hemicycliophora species andHemicriconemoides species; Hirshmanniella species; Lance nematodes,Hoploaimus species; false rootknot nematodes, Nacobbus species; Needlenematodes, Longidorus elongatus and other Longidorus species; Lesionnematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchuscurvitatus, Pratylenchus goodeyi and other Pratylenchus species;Burrowing nematodes, Radopholus similis and other Radopholus species;Reniform nematodes, Rotylenchus robustus and other Rotylenchus species;Scutellonema species; Stubby root nematodes, Trichodorus primitivus andother Trichodorus species, Paratrichodorus species; Stunt nematodes,Tylenchorhynchus claytoni, Tylenchorhynchus dubius and otherTylenchorhynchus species; Citrus nematodes, Tylenchulus species; Daggernematodes, Xiphinema species; and other plant parasitic nematodespecies.

Compounds of the formula I are particularly useful for controllinginsects, preferably sucking or piercing insects such as insects from thegenera Thysanoptera, Hymenoptera, Orthoptera and Hemiptera, inparticular the following species:

Thysanoptera: Frankliniella fusca, Frankliniella occidentalis,Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmiand Thrips tabaci,

Hymenoptera: Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana,Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis,Solenopsis geminata and Solenopsis invicta,

Orthoptera: Acheta domestica, Blatta orientalis, Blattella germanica,Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria,Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus,Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata,Periplaneta americana, Schistocerca americana, Schistocerca peregrina,Stauronotus maroccanus and Tachycines asynamorus;

Hemiptera, in particular aphids: Acyrthosiphon onobrychis, Adelgeslaricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi,Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola,Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Brachycauduscardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudusprunicola, Brevicoryne brassicae, Capitophorus horni, Cerosiphagossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusianordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthumpseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae,Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphumeuphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius,Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzuscerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens,Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psyllamali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis,Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphismali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae,Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii;

Compounds of the formula I are particularly useful for controllinginsects of the orders Hemiptera and Thysanoptera and more preferably forcontrolling aphids.

Formulations

For use in a method according to the present invention, the compounds Ican be converted into the customary formulations, e.g. solutions,emulsions, suspensions, dusts, powders, pastes, granules and directlysprayable solutions. The use form depends on the particular purpose andapplication method. Formulations and application methods are chosen toensure in each case a fine and uniform distribution of the compound ofthe formula I according to the present invention.

The formulations are prepared in a known manner (see e.g. for reviewU.S. Pat. No. 3,060,084, EP-A 707 445 (for liquid concentrates),Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48,Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York,1963, pages 8-57 and et seq. WO 91/13546, U.S. Pat. No. 4,172,714, U.S.Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, U.S. Pat. No. 5,180,587,U.S. Pat. No. 5,232,701, U.S. Pat. No. 5,208,030, GB 2,095,558, U.S.Pat. No. 3,299,566, Klingman, Weed Control as a Science, John Wiley andSons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H.,Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim(Germany), 2001, 2. D. A. Knowles, Chemistry and Technology ofAgrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998(ISBN 0-7514-0443-8), for example by extending the active compound withauxiliaries suitable for the formulation of agrochemicals, such assolvents and/or carriers, if desired emulsifiers, surfactants anddispersants, preservatives, anti-foaming agents, anti-freezing agents,for seed treatment formulation also optionally colorants and/or bindersand/or gelling agents.

Solvents/carriers, which are suitable, are e.g.:

-   -   solvents such as water, aromatic solvents (for example Solvesso        products, xylene and the like), paraffins (for example mineral        fractions), alcohols (for example methanol, butanol, pentanol,        benzyl alcohol), ketones (for example cyclohexanone,        gamma-butyrolactone), pyrrolidones (N-methyl-pyrrolidone (NMP),        N-octylpyrrolidone NOP), acetates (glycol diacetate), alkyl        lactates, lactones such as g-butyrolactone, glycols, fatty acid        dimethylamides, fatty acids and fatty acid esters,        triglycerides, oils of vegetable or animal origin and modified        oils such as alkylated plant oils. In principle, solvent        mixtures may also be used.    -   carriers such as ground natural minerals and ground synthetic        minerals, such as silica gels, finely divided silicic acid,        silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole,        loess, clay, dolomite, diatomaceous earth, calcium sulfate and        magnesium sulfate, magnesium oxide, ground synthetic materials,        fertilizers, such as, for example, ammonium sulfate, ammonium        phosphate, ammonium nitrate, ureas and products of vegetable        origin, such as cereal meal, tree bark meal, wood meal and        nutshell meal, cellulose powders and other solid carriers.

Suitable emulsifiers are nonionic and anionic emulsifiers (for examplepolyoxyethylene fatty alcohol ethers, alkylsulfonates andarylsulfonates).

Examples of dispersants are lignin-sulfite waste liquors andmethylcellulose.

Suitable surfactants are alkali metal, alkaline earth metal and ammoniumsalts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonicacid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids andsulfated fatty alcohol glycol ethers, furthermore condensates ofsulfonated naphthalene and naphthalene derivatives with formaldehyde,condensates of naphthalene or of naphthalenesulfonic acid with phenoland formaldehyde, polyoxyethylene octylphenyl ether, ethoxylatedisooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers,tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether,alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxidecondensates, ethoxylated castor oil, polyoxyethylene alkyl ethers,ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal,sorbitol esters,

Also anti-freezing agents such as glycerin, ethylene glycol, propyleneglycol and bactericides such as can be added to the formulation.

Suitable antifoaming agents are for example antifoaming agents based onsilicon or magnesium stearate.

Suitable preservatives are for example dichlorophen und benzyl alcoholhemiformal

Suitable thickeners are compounds which confer a pseudoplastic flowbehavior to the formulation, i.e. high viscosity at rest and lowviscosity in the agitated stage. Mention may be made, in this context,for example, of commercial thickeners based on polysaccharides, such asXanthan Gum® (Kelzan® from Kelco), Rhodopol®23 (Rhone Poulenc) orVeegum® (from R. T. Vanderbilt), or organic phyllosilicates, such asAttaclay® (from Engelhardt). Antifoam agents suitable for thedispersions according to the invention are, for example, siliconeemulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® fromRhodia), long-chain alcohols, fatty acids, organofluorine compounds andmixtures thereof. Biocides can be added to stabilize the compositionsaccording to the invention against attack by microorganisms. Suitablebiocides are, for example, based on isothiazolones such as the compoundsmarketed under the trademarks Proxel® from Avecia (or Arch) or Acticide®RS from Thor Chemie and Kathon® MK from Rohm & Haas. Suitable antifreezeagents are organic polyols, for example ethylene glycol, propyleneglycol or glycerol. These are usually employed in amounts of not morethan 10% by weight, based on the total weight of the active compoundcomposition. If appropriate, the active compound compositions accordingto the invention may comprise 1 to 5% by weight of buffer, based on thetotal amount of the formulation prepared, to regulate the pH, the amountand type of the buffer used depending on the chemical properties of theactive compound or the active compounds. Examples of buffers are alkalimetal salts of weak inorganic or organic acids, such as, for example,phosphoric acid, boronic acid, acetic acid, propionic acid, citric acid,fumaric acid, tartaric acid, oxalic acid and succinic acid.

Substances which are suitable for the preparation of directly sprayablesolutions, emulsions, pastes or oil dispersions are mineral oilfractions of medium to high boiling point, such as kerosene or dieseloil, furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, for example toluene,xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or theirderivatives, methanol, ethanol, propanol, butanol, cyclohexanol,cyclohexanone, isophorone, strongly polar solvents, for example dimethylsulfoxide, N-methylpyrrolidone and water.

Powders, materials for spreading and dusts can be prepared by mixing orconcomitantly grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active ingredientsto solid carriers. Examples of solid carriers are mineral earths such assilica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk,bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate,magnesium sulfate, magnesium oxide, ground synthetic materials,fertilizers, such as, for example, ammonium sulfate, ammonium phosphate,ammonium nitrate, ureas, and products of vegetable origin, such ascereal meal, tree bark meal, wood meal and nutshell meal, cellulosepowders and other solid carriers.

In general, the formulations comprise from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the active ingredient. Theactive ingredients are employed in a purity of from 90% to 100%,preferably 95% to 100% (according to NMR spectrum).

For seed treatment purposes, respective formulations can be diluted 2-10fold leading to concentrations in the ready to use preparations of 0.01to 60% by weight active compound by weight, preferably 0.1 to 40% byweight.

The compound of formula I can be used as such, in the form of theirformulations or the use forms prepared therefrom, for example in theform of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dustable products,materials for spreading, or granules, by means of spraying, atomizing,dusting, spreading or pouring. The use forms depend entirely on theintended purposes; they are intended to ensure in each case the finestpossible distribution of the active compounds according to theinvention.

The following are examples of formulations:

-   1. Products for dilution with water. For seed treatment purposes,    such products may be applied to the seed diluted or undiluted.    A) Water-Soluble Concentrates (SL, LS)

10 parts by weight of the active compound is dissolved in 90 parts byweight of water or a water-soluble solvent. As an alternative, wettersor other auxiliaries are added. The active compound dissolves upondilution with water, whereby a formulation with 10% (w/w) of activecompound is obtained.

B) Dispersible Concentrates (DC)

20 parts by weight of the active compound is dissolved in 70 parts byweight of cyclohexanone with addition of 10 parts by weight of adispersant, for example polyvinylpyrrolidone. Dilution with water givesa dispersion, whereby a formulation with 20% (w/w) of active compoundsis obtained.

C) Emulsifiable Concentrates (EC)

15 parts by weight of the active compounds is dissolved in 7 parts byweight of xylene with addition of calcium dodecylbenzenesulfonate andcastor oil ethoxylate (in each case 5 parts by weight). Dilution withwater gives an emulsion, whereby a formulation with 15% (w/w) of activecompounds is obtained.

D) Emulsions (EW, EO, ES)

25 parts by weight of the active compound is dissolved in 35 parts byweight of xylene with addition of calcium dodecylbenzenesulfonate andcastor oil ethoxylate (in each case 5 parts by weight). This mixture isintroduced into 30 parts by weight of water by means of an emulsifiermachine (e.g. Ultraturrax) and made into a homogeneous emulsion.Dilution with water gives an emulsion, whereby a formulation with 25%(w/w) of active compound is obtained.

E) Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of the active compound iscomminuted with addition of 10 parts by weight of dispersants, wettersand 70 parts by weight of water or of an organic solvent to give a fineactive compound suspension. Dilution with water gives a stablesuspension of the active compound, whereby a formulation with 20% (w/w)of active compound is obtained.

F) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50 parts by weight of the active compound is ground finely with additionof 50 parts by weight of dispersants and wetters and made aswater-dispersible or water-soluble granules by means of technicalappliances (for example extrusion, spray tower, fluidized bed). Dilutionwith water gives a stable dispersion or solution of the active compound,whereby a formulation with 50% (w/w) of active compound is obtained.

G) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, SS, WS)

75 parts by weight of the active compound are ground in a rotor-statormill with addition of 25 parts by weight of dispersants, wetters andsilica gel. Dilution with water gives a stable dispersion or solution ofthe active compound, whereby a formulation with 75% (w/w) of activecompound is obtained.

H) Gel-Formulation (GF)

In an agitated ball mill, 20 parts by weight of the active compound iscomminuted with addition of 10 parts by weight of dispersants, 1 part byweight of a gelling agent wetters and 70 parts by weight of water or ofan organic solvent to give a fine active compound suspension. Dilutionwith water gives a stable suspension of the active compound, whereby aformulation with 20% (w/w) of active compound is obtained.

-   2. Products to be applied undiluted for foliar applications. For    seed treatment purposes, such products may be applied to the seed    diluted or undiluted.    I) Dustable Powders (DP, DS)

5 parts by weight of the active compound are ground finely and mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dustable product having 5% (w/w) of active compound.

J) Granules (GR, FG, GG, MG)

0.5 part by weight of the active compound is ground finely andassociated with 95.5 parts by weight of carriers, whereby a formulationwith 0.5% (w/w) of active compound is obtained. Current methods areextrusion, spray-drying or the fluidized bed. This gives granules to beapplied undiluted for foliar use.

K) ULV Solutions (UL)

10 parts by weight of the active compound is dissolved in 90 parts byweight of an organic solvent, for example xylene. This gives a producthaving 10% (w/w) of active compound, which is applied undiluted forfoliar use.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwettable powders (sprayable powders, oil dispersions) by adding water.To prepare emulsions, pastes or oil dispersions, the substances, as suchor dissolved in an oil or solvent, can be homogenized in water by meansof a wetter, tackifier, dispersant or emulsifier. Alternatively, it ispossible to prepare concentrates composed of active substance, wetter,tackifier, dispersant or emulsifier and, if appropriate, solvent or oil,and such concentrates are suitable for dilution with water.

The active ingredient concentrations in the ready-to-use products can bevaried within relatively wide ranges. In general, they are from 0.0001to 10%, preferably from 0.01 to 1%.

The active ingredients may also be used successfully in theultra-low-volume process (ULV), it being possible to apply formulationscomprising over 95% by weight of active ingredient, or even to apply theactive ingredient without additives.

In the method of this invention compounds I may be applied with otheractive ingredients, for example with other pesticides, insecticides,herbicides, fertilizers such as ammonium nitrate, urea, potash, andsuperphosphate, phytotoxicants and plant growth regulators, safeners andnematicides. These additional ingredients may be used sequentially or incombination with the above-described compositions, if appropriate alsoadded only immediately prior to use (tank mix). For example, theplant(s) may be sprayed with a composition of this invention eitherbefore or after being treated with other active ingredients.

The following list M of pesticides together with which the compoundsaccording to the invention can be used and with which potentialsynergistic effects might be produced, is intended to illustrate thepossible combinations, but not to impose any limitation:

-   M.1. Organo(thio)phosphates: acephate, azamethiphos, azinphos-ethyl,    azinphosmethyl, chlorethoxyfos, chlorfenvinphos, chlormephos,    chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos,    demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos,    dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos,    famphur, fenamiphos, fenitrothion, fenthion, flupyrazophos,    fosthiazate, heptenophos, isoxathion, malathion, mecarbam,    methamidophos, methidathion, mevinphos, monocrotophos, naled,    omethoate, oxydemeton-methyl, parathion, parathion-methyl,    phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,    pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos,    pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos,    terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon,    vamidothion;-   M.2. Carbamates: aldicarb, alanycarb, bendiocarb, benfuracarb,    butocarboxim, butoxy-carboxim, carbaryl, carbofuran, carbosulfan,    ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,    methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, pro-poxur,    thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate;-   M.3. Pyrethroids: acrinathrin, allethrin, d-cis-trans allethrin,    d-trans allethrin, bifenthrin, bioallethrin, bioallethrin    S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-,    yfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,    cypermethrin, alpha-cypermethrin, beta-cypermethrin,    theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin,    empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate,    flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin,    permethrin, phenothrin, prallethrin, resmethrin, RU 15525,    silafluofen, tefluthrin, tetramethrin, tralomethrin, transfluthrin,    ZXI 8901;-   M.4. Juvenile hormone mimics: hydroprene, kinoprene, methoprene,    fenoxycarb, pyriproxyfen;-   M.5. Nicotinic receptor agonists/antagonists compounds: acetamiprid,    bensultap, cartap hydrochloride, clothianidin, dinotefuran,    imidacloprid, thiamethoxam, nitenpyram, nicotine, spinosad    (allosteric agonist), thiacloprid, thiocyclam, thiosultap-sodium and    AKD1022.-   M.6. GABA gated chloride channel antagonist compounds: chlordane,    endosulfan, gamma-HCH (lindane); acetoprole, ethiprole, fipronil,    pyrafluprole, pyriprole, vaniliprole, the phenylpyrazole compound of    formula M^(6.1)

-   M.7. Chloride channel activators: abamectin, emamectin benzoate,    milbemectin, lepimectin;-   M.8. METI I compounds: fenazaquin, fenpyroximate, pyrimidifen,    pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, rotenone;-   M.9. METI II and III compounds: acequinocyl, fluacyprim,    hydramethylnon;-   M.10. Uncouplers of oxidative phosphorylation: chlorfenapyr, DNOC;-   M.11. Inhibitors of oxidative phosphorylation: azocyclotin,    cyhexatin, diafenthiuron, fenbutatin oxide, propargite, tetradifon;-   M.12. Moulting disruptors: cyromazine, chromafenozide, halofenozide,    methoxyfenozide, tebufenozide;-   M.13. Synergists: piperonyl butoxide, tribufos;-   M.14. Sodium channel blocker compounds: indoxacarb, metaflumizone;-   M.15. Fumigants: methyl bromide, chloropicrin sulfuryl fluoride;-   M.16. Selective feeding blockers: crylotie, pymetrozine, flonicamid;-   M.17. Mite growth inhibitors: clofentezine, hexythiazox, etoxazole;-   M.18. Chitin synthesis inhibitors: buprofezin, bistrifluoron,    chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron,    hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron,    triflumuron;-   M.19. Lipid biosynthesis inhibitors: spirodiclofen, spiromesifen,    spirotetramat;-   M.20. octapaminergic agonsits: amitraz;-   M.21. ryanodine receptor modulators: flubendiamide;-   M.22. Various: aluminium phosphide, amidoflumet, benclothiaz,    benzoximate, bifenazate, borax, bromopropylate, cyanide,    cyenopyrafen, cyflumetofen, chinomethionate, dicofol, fluoroacetate,    phosphine, pyridalyl, pyrifluquinazon, sulfur, organic sulfur    compounds, tartar emetic; pyrimidinyl alkynylether compounds    M^(22.1) or thiadiazolyl alkynylether compounds M^(22.2):

wherein R^(M-22) is methyl or ethyl and Het* is3,3-dimethylpyrrolidin-1-yl, 3-methylpiperidin-1-yl,3,5-dimethylpiperidin-1-yl, 3-trifluormethylpiperidin-1-yl,hexa-hydroazepin-1-yl, 2,6-dimethylhexahydroazepin-1-yl or2,6-dimethylmorpholin-4-yl.

-   M.23.    N—R′-2,2-dihalo-1-R″cyclo-propanecarboxamide-2-(2,6-dichloro-α,α,α-tri-fluorop-tolyl)hydrazone    or    N—R′-2,2-di(R′″)propionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-hydrazone,    wherein R′ is methyl or ethyl, halo is chloro or bromo, R″ is    hydrogen or methyl and R′″ is methyl or ethyl;-   M.24. Anthranilamides: chloranthraniliprole, the compound of formula    M²⁴ 1

-   M.25. Malononitrile compounds: CF₂HCF₂CF₂CF₂CH₂C(CN)₂CH₂CH₂CF₃    (2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,3-trifluoro-propyl)malononitrile),    CF₃(CH₂)₂C(CN)₂CH₂(CF₂)₅CF₂H,    (2-(2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-heptyl)-2-(3,3,3-trifluoro-propyl)-malononitrile),    CF₃(CH₂)₂C(CN)₂(CH₂)₂C(CF₃)₂F    (2-(3,4,4,4-Tetrafluoro-3-trifluoromethyl-butyl)-2-(3,3,3-trifluoro-propyl)-malononitrile),    CF₃(CH₂)₂C(CN)₂(CH₂)₂(CF₂)₃CF₃    (2-(3,3,4,4,5,5,6,6,6-Nonafluoro-hexyl)-2-(3,3,3-trifluoro-propyl)-malononitrile),    CF₂H(CF₂)₃CH₂C(CN)₂CH₂(CF₂)₃CF₂H    (2,2-Bis-(2,2,3,3,4,4,5,5-octafluoro-pentyl)-malononitrile),    CF₃(CH₂)₂C(CN)₂CH₂(CF₂)₃CF₃    (2-(2,2,3,3,4,4,5,5,5-Nonafluoro-pentyl)-2-(3,3,3-trifluoro-propyl)-malononitrile),    CF₃(CF₂)₂CH₂C(CN)₂CH₂(CF₂)₃CF₂H    (2-(2,2,3,3,4,4,4-Heptafluoro-butyl)-2-(2,2,3,3,4,4,5,5-octafluoro-pentyl)-malononitrile),    CF₃CF₂CH₂C(CN)₂CH₂(CF₂)₃CF₂H    (2-(2,2,3,3,4,4,5,5-Octafluoro-pentyl)-2-(2,2,3,3,3-pentafluoro-propyl)-malononitrile),    CF₂HCF₂CF₂CF₂CH₂C(CN)₂CH₂CH₂CF₂CF₃    (2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,4,4,4-pentafluorobutyl)-malonodinitrile),    CF₃(CH₂)₂C(CN)₂CH₂(CF₂)₃CF₂H    (2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,3-trifluoro-butyl)-malononitrile);-   M.26. Microbial disruptors: Bacillus thuringiensis subsp.    Israelensi, Bacillus sphaericus, Bacillus thuringiensis subsp.    Aizawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus    thuringiensis subsp. Tenebrionis;

The commercially available compounds of the group M may be found in ThePesticide Manual, 13^(th) Edition, British Crop Protection Council(2003) among other publications.

Thioamides of formula M^(6.1) and their preparation have been describedin WO 98/28279. Lepimectin is known from Agro Project, PJB PublicationsLtd, November 2004. Benclothiaz and its preparation have been describedin EP-A1 454621. Methidathion and Paraoxon and their preparation havebeen described in Farm Chemicals Handbook, Volume 88, Meister PublishingCompany, 2001. Acetoprole and its preparation have been described in WO98/28277. Metaflumizone and its preparation have been described in EP-A1462 456. Flupyrazofos has been described in Pesticide Science 54, 1988,p. 237-243 and in U.S. Pat. No. 4,822,779. Pyrafluprole and itspreparation have been described in JP 2002193709 and in WO 01/00614.Pyriprole and its preparation have been described in WO 98/45274 and inU.S. Pat. No. 6,335,357. Amidoflumet and its preparation have beendescribed in U.S. Pat. No. 6,221,890 and in JP 21010907. Flufenerim andits preparation have been described in WO 03/007717 and in WO 03/007718.AKD 1022 and its preparation have been described in U.S. Pat. No.6,300,348. Chloranthraniliprole has been described in WO 01/70671, WO03/015519 and WO 05/118552. Anthranilamide derivatives of formulaM^(24.1) have been described in WO 01/70671, WO 04/067528 and WO05/118552. Cyflumetofen and its preparation have been described in WO04/080180. The aminoquinazolinone compound pyrifluquinazon has beendescribed in EP A 109 7932. The alkynylether compounds M^(22.1) andM^(22.2) are described e.g. in JP 2006131529. Organic sulfur compoundshave been described in WO 2007060839. The malononitrile compounds havebeen described in WO 02/089579, WO 02/090320, WO 02/090321, WO04/006677, WO 05/068423, WO 05/068432 and WO 05/063694.

Fungicidal mixing partners are those selected from the group Fconsisting of

-   F.1 acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl;-   F.2 amine derivatives such as aldimorph, dodine, dodemorph,    fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamin,    tridemorph;-   F.3 anilinopyrimidines such as pyrimethanil, mepanipyrim or    cyrodinyl;-   F.4 antibiotics such as cycloheximid, griseofulvin, kasugamycin,    natamycin, polyoxin or streptomycin;-   F.5 azoles such as bitertanol, bromoconazole, cyproconazole,    difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole,    fluquiconazole, flusilazole, hexaconazole, imazalil, metconazole,    myclobutanil, penconazole, propiconazole, prochloraz,    prothioconazole, tebuconazole, triadimefon, triadimenol,    triflumizol, triticonazole, flutriafol;-   F.6 dicarboximides such as iprodion, myclozolin, procymidon,    vinclozolin;-   F.7 dithiocarbamates such as ferbam, nabam, maneb, mancozeb, metam,    metiram, propineb, polycarbamate, thiram, ziram, zineb;-   F.8 heterocyclic compounds such as anilazine, benomyl, boscalid,    carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon,    famoxadon, fenamidon, fenarimol, fuberidazole, flutolanil,    furametpyr, isoprothiolane, mepronil, nuarimol, probenazole,    proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam,    thiabendazole, thifluzamid, thiophanate-methyl, tiadinil,    tricyclazole, triforine;-   F.9 copper fungicides such as Bordeaux mixture, copper acetate,    copper oxychloride, basic copper sulfate;-   F.10 nitrophenyl derivatives such as binapacryl, dinocap, dinobuton,    nitrophthalisopropyl;-   F.11 phenylpyrroles such as fenpiclonil or fludioxonil;-   F.12 strobilurins such as azoxystrobin, dimoxystrobin,    fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin,    picoxystrobin or trifloxystrobin;-   F.13 sulfenic acid derivatives such as captafol, captan,    dichlofluanid, folpet, tolylfluanid;-   F.14 cinnemamides and analogs such as dimethomorph, flumetover or    flumorph;-   F.15 sulfur, and other fungicides such as acibenzolar-S-methyl,    benthiavalicarb, carpropamid, chlorothalonil, cyflufenamid,    cymoxanil, dazomet, diclomezin, diclocymet, diethofencarb,    edifenphos, ethaboxam, fenhexamid, fentin-acetate, fenoxanil,    ferimzone, fluazinam, fosetyl, fosetyl-aluminum, iprovalicarb,    hexachlorobenzene, metrafenon, pencycuron, propamocarb, phthalide,    toloclofos-methyl, quintozene, zoxamid.    Applications

The animal pest, i.e. the insects, arachnids and nematodes, the plant,soil or water in which the plant is growing can be contacted with thepresent compound(s) I or composition(s) containing them by anyapplication method known in the art. As such, “contacting” includes bothdirect contact (applying the compounds/compositions directly on theanimal pest or plant—typically to the foliage, stem or roots of theplant) and indirect contact (applying the compounds/compositions to thelocus of the animal pest or plant).

The compounds of formula I or the pesticidal compositions comprisingthem may be used to protect growing plants and crops from attack orinfestation by animal pests, especially insects, acaridae or arachnidsby contacting the plant/crop with a pesticidally effective amount ofcompounds of formula I. The term “crop” refers both to growing andharvested crops.

Moreover, animal pests may be controlled by contacting the target pest,its food supply, habitat, breeding ground or its locus with apesticidally effective amount of compounds of formula I. As such, theapplication may be carried out before or after the infection of thelocus, growing crops, or harvested crops by the pest.

The compounds of the invention can also be applied preventively toplaces at which occurrence of the pests is expected.

The compounds of formula I may be also used to protect growing plantsfrom attack or infestation by pests by contacting the plant with apesticidally effective amount of compounds of formula I. As such,“contacting” includes both direct contact (applying thecompounds/compositions directly on the pest and/or plant—typically tothe foliage, stem or roots of the plant) and indirect contact (applyingthe compounds/compositions to the locus of the pest and/or plant).

“Locus” means a habitat, breeding ground, plant, seed, soil, area,material or environment in which a pest or parasite is growing or maygrow.

In general, “pesticidally effective amount” means the amount of activeingredient needed to achieve an observable effect on growth, includingthe effects of necrosis, death, retardation, prevention, and removal,destruction, or otherwise diminishing the occurrence and activity of thetarget organism. The pesticidally effective amount can vary for thevarious compounds/compositions used in the invention. A pesticidallyeffective amount of the compositions will also vary according to theprevailing conditions such as desired pesticidal effect and duration,weather, target species, locus, mode of application, and the like.

In the case of soil treatment or of application to the pests dwellingplace or nest, the quantity of active ingredient ranges from 0.0001 to500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

Customary application rates in the protection of materials are, forexample, from 0.01 g to 1000 g of active compound per m² treatedmaterial, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materialstypically contain from 0.001 to 95 weight %, preferably from 0.1 to 45weight %, and more preferably from 1 to 25 weight % of at least onerepellent and/or insecticide.

For use in treating crop plants, the rate of application of the activeingredients of this invention may be in the range of 0.1 g to 4000 g perhectare, desirably from 25 g to 600 g per hectare, more desirably from50 g to 500 g per hectare.

The compounds of formula I are effective through both contact (via soil,glass, wall, bed net, carpet, plant parts or animal parts), andingestion (bait, or plant part).

The compounds of the invention may also be applied against non-cropinsect pests, such as ants, termites, wasps, flies, mosquitos, crickets,or cockroaches. For use against said non-crop pests, compounds offormula I are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. agel). Solid baits can be formed into various shapes and forms suitableto the respective application e.g. granules, blocks, sticks, disks.Liquid baits can be filled into various devices to ensure properapplication, e.g. open containers, spray devices, droplet sources, orevaporation sources. Gels can be based on aqueous or oily matrices andcan be formulated to particular necessities in terms of stickyness,moisture retention or aging characteristics.

The bait employed in the composition is a product, which is sufficientlyattractive to incite insects such as ants, termites, wasps, flies,mosquitos, crickets etc. or cockroaches to eat it. The attractivenesscan be manipulated by using feeding stimulants or sex pheromones. Foodstimulants are chosen, for example, but not exclusively, from animaland/or plant proteins (meat-, fish- or blood meal, insect parts, eggyolk), from fats and oils of animal and/or plant origin, or mono-,oligo- or polyorganosaccharides, especially from sucrose, lactose,fructose, dextrose, glucose, starch, pectin or even molasses or honey.Fresh or decaying parts of fruits, crops, plants, animals, insects orspecific parts thereof can also serve as a feeding stimulant. Sexpheromones are known to be more insect specific. Specific pheromones aredescribed in the literature and are known to those skilled in the art.

For use in bait compositions, the typical content of active ingredientis from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to5% weight % of active compound.

Formulations of compounds of formula I as aerosols (e.g. in spray cans),oil sprays or pump sprays are highly suitable for the non-professionaluser for controlling pests such as flies, fleas, ticks, mosquitos orcockroaches. Aerosol recipes are preferably composed of the activecompound, solvents such as lower alcohols (e.g. methanol, ethanol,propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone),paraffin hydrocarbons (e.g. kerosenes) having boiling ranges ofapproximately 50 to 250° C., dimethylformamide, N-methylpyrrolidone,dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene,water, furthermore auxiliaries such as emulsifiers such as sorbitolmonooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fattyalcohol ethoxylate, perfume oils such as ethereal oils, esters of mediumfatty acids with lower alcohols, aromatic carbonyl compounds, ifappropriate stabilizers such as sodium benzoate, amphoteric surfactants,lower epoxides, triethyl orthoformate and, if required, propellants suchas propane, butane, nitrogen, compressed air, dimethyl ether, carbondioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that nopropellants are used.

For use in spray compositions, the content of active ingredient is from0.001 to 80 weights %, preferably from 0.01 to 50 weight % and mostpreferably from 0.01 to 15 weight %.

The compounds of formula I and its respective compositions can also beused in mosquito and fumigating coils, smoke cartridges, vaporizerplates or long-term vaporizers and also in moth papers, moth pads orother heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g.malaria, dengue and yellow fever, lymphatic filariasis, andleishmaniasis) with compounds of formula I and its respectivecompositions also comprise treating surfaces of huts and houses, airspraying and impregnation of curtains, tents, clothing items, bed nets,tsetse-fly trap or the like. Insecticidal compositions for applicationto fibers, fabric, knitgoods, nonwovens, netting material or foils andtarpaulins preferably comprise a mixture including the insecticide,optionally a repellent and at least one binder. Suitable repellents forexample are N,N-Diethyl-meta-toluamide (DEET),N,N-diethylphenylacetamide (DEPA),1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine,(2-hydroxymethylcyclohexyl)acetic acid lactone, 2-ethyl-1,3-hexandiol,indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insectcontrol such as{(+/−)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)trans-chrysantemate(Esbiothrin), a repellent derived from or identical with plant extractslike limonene, eugenol, (+)-Eucamalol (1), (−)-1-epi-eucamalol or crudeplant extracts from plants like Eucalyptus maculata, Vitex rotundifolia,Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogannartdus (citronella). Suitable binders are selected for example frompolymers and copolymers of vinyl esters of aliphatic acids (such as suchas vinyl acetate and vinyl versatate), acrylic and methacrylic esters ofalcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methylacrylate, mono- and di-ethylenically unsaturated hydrocarbons, such asstyrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dippingthe textile material into emulsions or dispersions of the insecticide orspraying them onto the nets.

The compounds of formula I and its compositions can be used forprotecting wooden materials such as trees, board fences, sleepers, etc.and buildings such as houses, outhouses, factories, but alsoconstruction materials, furniture, leathers, fibers, vinyl articles,electric wires and cables etc. from ants and/or termites, and forcontrolling ants and termites from doing harm to crops or human being(e.g. when the pests invade into houses and public facilities). Thecompounds of formula I are applied not only to the surrounding soilsurface or into the under-floor soil in order to protect woodenmaterials but it can also be applied to lumbered articles such assurfaces of the under-floor concrete, alcove posts, beams, plywoods,furniture, etc., wooden articles such as particle boards, half boards,etc. and vinyl articles such as coated electric wires, vinyl sheets,heat insulating material such as styrene foams, etc. In case ofapplication against ants doing harm to crops or human beings, the antcontroller of the present invention is applied to the crops or thesurrounding soil, or is directly applied to the nest of ants or thelike.

Seed Treatment

The compounds of formula I are also suitable for the treatment of seedsin order to protect the seed from insect pest, in particular fromsoil-living insect pests and the resulting plant's roots and shootsagainst soil pests and foliar insects.

The compounds of formula I are particularly useful for the protection ofthe seed from soil pests and the resulting plant's roots and shootsagainst soil pests and foliar insects. The protection of the resultingplant's roots and shoots is preferred. More preferred is the protectionof resulting plant's shoots from piercing and sucking insects, whereinthe protection from aphids is most preferred.

The present invention therefore comprises a method for the protection ofseeds from insects, in particular from soil insects and of theseedlings' roots and shoots from insects, in particular from soil andfoliar insects, said method comprising contacting the seeds beforesowing and/or after pregermination with a compound of the generalformula I or a salt thereof. Particularly preferred is a method, whereinthe plant's roots and shoots are protected, more preferably a method,wherein the plants shoots are protected form piercing and suckinginsects, most preferably aa method, wherein the plants shoots areprotected from aphids.

The term seed embraces seeds and plant propagules of all kinds includingbut not limited to true seeds, seed pieces, suckers, corms, bulbs,fruit, tubers, grains, cuttings, cut shoots and the like and means in apreferred embodiment true seeds.

The term seed treatment comprises all suitable seed treatment techniquesknown in the art, such as seed dressing, seed coating, seed dusting,seed soaking and seed pelleting.

The present invention also comprises seeds coated with or containing theactive compound.

The term “coated with and/or containing” generally signifies that theactive ingredient is for the most part on the surface of the propagationproduct at the time of application, although a greater or lesser part ofthe ingredient may penetrate into the propagation product, depending onthe method of application. When the said propagation product is(re)planted, it may absorb the active ingredient.

Suitable seed is seed of cereals, root crops, oil crops, vegetables,spices, ornamentals, for example seed of durum and other wheat, barley,oats, rye, maize (fodder maize and sugar maize/sweet and field corn),soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice,oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes,grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash,cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species,melons, beans, peas, garlic, onions, carrots, tuberous plants such aspotatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums,pansies and impatiens.

In addition, the active compound may also be used for the treatmentseeds from plants, which tolerate the action of herbicides or fungicidesor insecticides owing to breeding, including genetic engineeringmethods.

For example, the active compound can be employed in treatment of seedsfrom plants, which are resistant to herbicides from the group consistingof the sulfonylureas, imidazolinones, glufosinate-ammonium orglyphosate-isopropylammonium and analogous active substances (see forexample, EP-A-0242236, EP-A-242246) (WO 92/00377) (EP-A-0257993, U.S.Pat. No. 5,013,659) or in transgenic crop plants, for example cotton,with the capability of producing Bacillus thuringiensis toxins (Bttoxins) which make the plants resistant to certain pests (EP-A-0142924,EP-A-0193259),

Furthermore, the active compound can be used also for the treatment ofseeds from plants, which have modified characteristics in comparisonwith existing plants consist, which can be generated for example bytraditional breeding methods and/or the generation of mutants, or byrecombinant procedures). For example, a number of cases have beendescribed of recombinant modifications of crop plants for the purpose ofmodifying the starch synthesized in the plants (e.g. WO 92/11376, WO92/14827, WO 91/19806) or of transgenic crop plants having a modifiedfatty acid composition (WO 91/13972).

The seed treatment application of the active compound is carried out byspraying or by dusting the seeds before sowing of the plants and beforeemergence of the plants.

Compositions which are especially useful for seed treatment are e.g.:

-   A Soluble concentrates (SL, LS)-   D Emulsions (EW, EO, ES)-   E Suspensions (SC, OD, FS)-   F Water-dispersible granules and water-soluble granules (WG, SG)-   G Water-dispersible powders and water-soluble powders (WP, SP, WS)-   H Gel-Formulations (GF)-   I Dustable powders (DP, DS)

Conventional seed treatment formulations include for example flowableconcentrates FS, solutions LS, powders for dry treatment DS, waterdispersible powders for slurry treatment WS, water-soluble powders SSand emulsion ES and EC and gel formulation GF. These formulations can beapplied to the seed diluted or undiluted. Application to the seeds iscarried out before sowing, either directly on the seeds or after havingpregerminated the latter

In a preferred embodiment a FS formulation is used for seed treatment.Typically, a FS formulation may comprise 1-800 g/l of active ingredient,1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l ofbinder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent,preferably water.

Especially preferred FS formulations of compounds of formula I for seedtreatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) ofthe active ingredient, from 0.1 to 20% by weight (1 to 200 g/l) of atleast one surfactant, e.g. 0.05 to 5% by weight of a wetter and from 0.5to 15% by weight of a dispersing agent, up to 20% by weight, e.g. from 5to 20% of an anti-freeze agent, from 0 to 15% by weight, e.g. 1 to 15%by weight of a pigment and/or a dye, from 0 to 40% by weight, e.g. 1 to40% by weight of a binder (sticker/adhesion agent), optionally up to 5%by weight, e.g. from 0.1 to 5% by weight of a thickener, optionally from0.1 to 2% of an anti-foam agent, and optionally a preservative such as abiocide, antioxidant or the like, e.g. in an amount from 0.01 to 1% byweight and a filler/vehicle up to 100% by weight.

Seed Treatment formulations may additionally also comprise binders andoptionally colorants.

Binders can be added to improve the adhesion of the active materials onthe seeds after treatment. Suitable binders are homo- and copolymersfrom alkylene oxides like ethylene oxide or propylene oxide,polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, andcopolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- andcopolymers, polyethyleneamines, polyethyleneamides andpolyethyleneimines, polysaccharides like celluloses, tylose and starch,polyolefin homo- and copolymers like olefin/maleic anhydride copolymers,polyurethanes, polyesters, polystyrene homo and copolymers

Optionally, also colorants can be included in the formulation. Suitablecolorants or dyes for seed treatment formulations are Rhodamin B, C.I.Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigmentyellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigmentred 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigmentorange 34, pigment orange 5, pigment green 36, pigment green 7, pigmentwhite 6, pigment brown 25, basic violet 10, basic violet 49, acid red51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10,basic red 108.

Examples of a Gelling Agent is Carrageen (Satiagel®)

In the treatment of seed, the application rates of the compounds I aregenerally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kgof seed and in particular from 1 g to 200 g per 100 kg of seed.

The invention therefore also relates to seed comprising a compound ofthe formula I, or an agriculturally useful salt of 1, as defined herein.The amount of the compound I or the agriculturally useful salt thereofwill in general vary from 0.1 g to 10 kg per 100 kg of seed, preferablyfrom 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 gper 100 kg of seed. For specific crops such as lettuce the rate can behigher.

The present invention is now illustrated in further details by thefollowing examples.

EXAMPLES

The present invention is now illustrated in further details by thefollowing examples.

Some of the preferred compound examples are characterized by theirphysical data in the following table C. The characterized is done bycoupled High Performance Liquid Chromatography/mass spectrometry(HPLC/MS), by NMR or by their melting points.

Analytical HPLC column: RP-18 column Chromolith Speed ROD from MerckKgaA, Germany). Elution: acetonitrile+0.1% trifluoroacetic acid(TFA)/water+0.1% trifluoroacetic acid (TFA) in a ratio of from 5:95 to95:5 in 5 minutes at 40° C. Alternatively the compounds wereadditionally or instead characterized by their melting point.

Some compounds were characterized by ¹H-NMR. The signals arecharacterized by chemical shift (ppm) vs. tetramethylsilane, by theirmultiplicity and by their integral (relative number of hydrogen atomsgiven). The following abbreviations are used to characterize themultiplicity of the signals: M=multiplett, q=quartett, t=triplett,d=doublet and s=singulett.

TABLE C melting HPLC-MS (t_(r) = retention time) Compound point orexample Structure of compound F_(p) [° C.] ¹H NMR (in CDCl₃): δ [ppm] 1.

t_(r) = 2.16 min, m/z = 295 [M + 23] 2.

t_(r) = 2.31 min, m/z = 305 [M + 1] 3.

t_(r) = 2.75 min, m/z = 255 [M + 1] 4.

t_(r) = 2.11 min, m/z = 257 [M + 1] 5.

t_(r) = 2.62 min, m/z = 251 [M + 1] 6.

t_(r) = 2.25 min, m/z = 245 [M + 1] 7.

t_(r) = 2.32 min, m/z = 237 [M + 1] 8.

t_(r) = 2.45 min, m/z = 241 [M + 1] 9.

t_(r) = 2.79 min, m/z = 255 [M + 1] 10.

t_(r) = 3.07 min, m/z = 269 [M + 1] 11.

t_(r) = 2.84 min, m/z = 267 [M + 1] 12.

t_(r) = 3.39 min, m/z = 295 [M + 1] 13.

t_(r) = 3.08 min, m/z = 269 [M + 1] 14.

t_(r) = 3.39 min, m/z = 317 [M + 1] 15.

t_(r) = 3.35 min, m/z = 283 [M + 1] 16.

t_(r) = 3.12 min, m/z = 281 [M + 1] 17.

t_(r) = 3.14 min, m/z = 303 [M + 1] 18.

t_(r) = 2.06 min, m/z = 291 [M + 1] 19.

t_(r) = 3.69 min, m/z = 309 [M + 1] 20.

t_(r) = 2.93 min, m/z = 301 [M + 1] 21.

t_(r) = 3.14 min, m/z = 327 [M + 1] 22.

t_(r) = 2.86 min, m/z = 301 [M + 1] 23.

t_(r) = 3.28 min, m/z = 349 [M + 1] 24.

t_(r) = 3.15 min, m/z = 315 [M + 1] 25.

t_(r) = 2.53 min, m/z = 273 [M + 1] 26.

t_(r) = 2.62 min, m/z = 341 [M + 1] 27.

t_(r) = 2.84 min, m/z = 287 [M + 1] 28.

t_(r) = 2.35 min, m/z = 327 [M + 1] 29.

t_(r) = 2.89 min, m/z = 299 [M + 1] 30.

t_(r) = 2.79 min, m/z = 287 [M + 1] 31.

t_(r) = 3.16 min, m/z = 335 [M + 1] 32.

t_(r) = 3.12 min, m/z = 313 [M + 1] 33.

¹H NMR (in CDCl₃): δ [ppm]= 1.04 (t, 3H), 1.20 (t, 3H), 1.89 (m, 1H),2.10 (m, 1H), 3.41 (m, 1H), 4.22 (m, 1H), 6.68 (t, 1H), 7.19 (t, 1H),7.57 (t, 1H), 7.75 (d, 1H) 34.

t_(r) = 3.12 min, m/z = 349 [M + 1] 35.

t_(r) = 2.95 min, m/z = 335 [M + 23] 36.

t_(r) = 2.63 min, m/z = 251 [M + 1] 37.

t_(r) = 2.95 min, m/z = 299 [M + 1] 38.

¹H NMR (in CDCl₃): δ [ppm] = 0.50 (m, 1H), 0.61 (m, 1H), 1.02 (m, 2H),3.30 (s, 3H), 3.92 (s, 3H), 6.79 (d, 1H), 7.48 (m, 2H) 39.

t_(r) = 2.90 min, m/z = 265 [M + 1] 40.

t_(r) = 3.17 min, m/z = 313 [M + 1] 41.

t_(r) = 3.07 min, m/z = 277 [M + 1] 42.

t_(r) = 2.89 min, m/z = 265 [M + 1] 43.

t_(r) = 3.12 min, m/z = 279 [M + 1] 44.

189-192 t_(r) = 2.32 min, m/z = 335 [M + 1] 45.

t_(r) = 2.00 min, m/z = 309 [M + 1] 46.

188-192 t_(r) = 2.35 min, m/z = 353 [M + 1] 47.

112-113 t_(r) = 2.75 min, m/z = 365 [M + 1] 48.

t_(r) = 2.27 min, m/z = 303 [M + 1] 49.

 95-97 50.

t_(r) = 1.80 min, m/z = 271 [M + 1] 51.

t_(r) = 2.04 min, m/z = 303 [M + 1] 52.

t_(r) = 1.90 min, m/z = 277 [M + 1] 53.

t_(r) = 2.44 min, m/z = 351 [M + 1] 54.

t_(r) = 2.35 min, m/z = 319 [M + 1] 55.

t_(r) = 2.49 min, m/z = 303 [M + 1] 56.

t_(r) = 2.74 min, m/z = 317 [M + 1] 57.

t_(r) = 3.03 min, m/z = 370 [M + 1] 58.

t_(r) = 3.26 min, m/z = 384 [M + 1] 59.

t_(r) = 2.39 min, m/z = 271 [M + 1] 60.

141-143° C. 61.

t_(r) = 2.97 min, m/z = 301 [M + 1] 62.

t_(r) = 3.06 min, m/z = 271 [M + 1] 63.

t_(r) = 3.35 min, m/z = 325 [M + 1] 64.

t_(r) = 2.95 min, m/z = 284 [M + 1] 65.

t_(r) = 2.34 min, m/z = 270 [M + 1] 66.

t_(r) = 3.17 min, m/z = 368 [M + 1] 67.

t_(r) = 2.97 min, m/z = 354 [M + 1] 68.

t_(r) = 2.88 min, m/z = 334 [M + 1] 69.

t_(r) = 2.97 min, m/z = 338 [M + 1] 70.

t_(r) = 3.23 min, m/z = 352 [M + 1] 71.

t_(r) = 3.23 min, m/z = 382 [M + 1] 72.

t_(r) = 3.31 min, m/z = 386 [M + 1] 73.

t_(r) = 3.11 min, m/z = 348 [M + 1] 74.

t_(r) = 3.2 min, m/z = 470 [M + 1] 75.

t_(r) = 3.5 min, m/z = 458 [M + 1] 76.

t_(r) = 2.49 min, m/z = 303 [M + 1] 77.

t_(r) = 2.74 min, m/z = 317 [M + 1] 78.

t_(r) = 3.49 min, m/z = 490 [M + 1] 79.

t_(r) = 2.81 min, m/z = 356 [M + 1] 80.

t_(r) = 3.66 min, m/z = 504 [M + 1] 81.

t_(r) = 3.83 min, m/z = 518 [M + 1] 82.

t_(r) = 3.03 min, m/z = 370 [M + 1] 83.

t_(r) = 3.24 min, m/z = 384 [M + 1] 84.

178-179 85.

117-120 86.

t_(r) = 3.87 min, m/z = 482 [M + 1] 87.

t_(r) = 2.39 min, m/z = 271 [M + 1] 88.

t_(r) = 3.27 min, m/z = 466 [M + 1] 89.

t_(r) = 3.27 min, m/z = 502 [M + 1] 90.

t_(r) = 2.89 min, m/z = 390 [M + 1] 91.

141-143 92.

t_(r) = 3.42 min, m/z = 516 [M + 1] 93.

t_(r) = 2.97 min, m/z = 301 [M + 1] 94.

¹H NMR (in CDCl₃): δ [ppm] = 3.32 (s, 3H), 3.93 (s, 3H), 5.51 (s, 1H),6.78 (d, 1H), 7.40 (m, 1H), 7.49 (m, 2H), 7.89 (d, 1H), 8.48 (d, 1H) 95.

t_(r) = 2.74 min, m/z = 320 [M + 1] 96.

t_(r) = 2.88 min, m/z = 334 [M + 1] 97.

t_(r) = 2.97 min, m/z = 338 [M + 1] 98.

t_(r) = 3.23 min, m/z = 352 [M + 1] 99.

t_(r) = 2.77 min, m/z = 354 [M + 1] 100.

t_(r) = 3.23 min, m/z = 382 [M + 1] 101.

t_(r) = 2.69 min, m/z = 358 [M + 1] 102.

t_(r) = 3.31 min, m/z = 386 [M + 1] 103.

t_(r) = 3.11 min, m/z = 348 [M + 1] 104.

t_(r) = 2.67 min, m/z = 324 [M + 1] 105.

t_(r) = 3.00 min, m/z = 368 [M + 1] 106.

t_(r) = 3.07 min, m/z = 372 [M + 1] 107.

t_(r) = 3.04 min, m/z = 358 [M + 1] 108.

t_(r) = 3.31 min, m/z = 372 [M + 1] 109.

t_(r) = 3.06 min, m/z = 372 [M + 1] 110.

t_(r) = 2.63 min, m/z = 304 [M + 1] 111.

t_(r) = 2.94 min, m/z = 324 [M + 1] 112.

t_(r) = 2.87 min, m/z = 309 [M + 1] 113.

t_(r) = 3.28 min, m/z = 438 [M + 1] 114.

t_(r) = 3.51 min, m/z = 458 [M + 1] 115.

t_(r) = 3.12 min, m/z = 392 [M + 1] 116.

t_(r) = 3.33 min, m/z = 392 [M + 1] 117.

t_(r) = 3.09 min, m/z = 372 [M + 1] 118.

t_(r) = 3.20 min, m/z = 315 [M + 1] 119.

t_(r) = 3.85 min, m/z = 538 [M + 1] 120.

t_(r) = 3.78 min, m/z = 458 [M + 1] 121.

t_(r) = 3.59 min, m/z = 460 [M + 1] 122.

t_(r) = 3.54 min, m/z = 504 [M + 1] 123.

t_(r) = 3.27 min, m/z = 514 [M + 1] 124.

t_(r) = 3.62 min, m/z = 550 [M + 1] 125.

t_(r) = 1.91 min, m/z = 241 [M + 1]

Synthesis Examples S.14-Difluoromethoxy-3-S-dimethyl-thionitroso-benzo[d]isothiazole1,1-dioxide [Compound example 45 (of table C)]

-   Step 1: S,S Dimethyl —S— Aminosulfonium mesitylenesulfonate was    prepared according to Y. Tamura et al, Tetrahedron, 1975, 31,    3035-3040.    -   3-Chloro-4-difluoromethoxy-benzo[d]isothiazole 1,1-dioxide was        prepared by adding 9.50 g (38.1 mmol)        4-Difluoromethoxy-saccharine, 6.8 g (57.0 mmol) thionyl chloride        and 0.4 ml dimethylformamid (DMF) to 50 ml 1,4-dioxane and        heating to reflux for 29 h. The mixture was cooled to room        temperature and all volatiles were removed by distillation. 9.3        g of the 3-Chloro-4-difluoromethoxy-benzo[d]isothiazole        1,1-dioxide compound were obtained as a crude product and used        in the next step without further purification.-   Step 2: 0.51 g (1.90 mmol)    3-Chloro-4-difluoromethoxy-benzo[d]isothiazole 1,1-dioxide was    dissolved in 15 ml dichloromethane at room temperature. 0.49 g    Huenig's base was added, followed by 1.05 g (3.80 mmol) S,S    Dimethyl-S-Aminosulfonium mesitylene-sulfonate. Stirring at room    temperature was continued overnight. The solvent was removed by    distillation and the residue was purified on silica (eluent:    cyclohexanes/ethyl acetate 1:1) to yield 155 mg (0.50 mmol) of    compound example 45 of table C.

S.2(4-Chloro-1,1-dioxo-1H-1lambda*6*-benzo[d]isothiazol-3-yl)-(1-oxo-tetrahydro-1lambda*6*-thiophen-1-ylidene)-amine[Compound example 54 (of table C)]

100 mg (0.33 mmol) of compound 5 (prepared in analogy to compound 2)were dissolved in 2.5 ml dichloromethane at room temperature. 50 mgtetrabutylammonium bromide, dissolved in 5 ml ethyl acetate, were added,followed by 10 ml of a 12.5 wt. % NaOCl-solution. Stirring at roomtemperature was continued for 72 h. Water was added and the layers wereseparated. The aqueous layer was extracted with ethyl acetate twice. Thecombined organic layers were dried over magnesium sulfate. The solventwas removed by distillation and the residue was purified on silica(eluent: cyclohexanes/ethyl acetate 1:2) to yield 20 mg (0.06 mmol) ofcompound 11.

S.3 N-Ethyl-N-(4-methoxy-benzo[d]isothiazol-3-yl)-acetamide [Compoundexample 5 (of table C)]

-   Step 1: 7.0 g (42 mmol) 4-Methoxy-benzo[d]isothiazole [Drug.Res.    30(II), 11 (1980), 1831-1838] were dissolved in 150 ml methyl glycol    and 4.7 g (85 mmol) sodium methylate were added at room temperature.    The mixture was heated at 80° C. for 4 h, then additional 2.4 g (42    mmol) sodium methylate were added and the mixture was stirred for    1 h. After 2 h and again after 4 h additional 2.4 g (42 mmol) sodium    methylate were added. The mixture was stirred overnight at room    temperature. The resulting sodium salt was used without further    purification.    -   82 g (1.3 mol) aqueous ethylamine (70%) was added to the        reaction mixture, the solution was cooled to 0-5° C. and 40 g        aqueous 12% sodium hypochlorite was added dropwise during 20        min. The mixture was stirred for 1 h at this temperature, then        water was added and the product was extracted into ethyl        acetate. The organic layer was dried over sodium sulfate, the        solvent was removed by distillation and the residue was purified        on silica (eluent: cyclohexanes/ethyl acetate) to yield 5.7 g        (27 mmol) of Ethyl-(4-methoxy-benzo[d]isothiazol-3-yl)-amine [¹H        NMR (in CDCl₃): δ [ppm]=1.32 (t, 3H), 3.58 (q, 2H), 3.98 (s,        3H), 6.28 (bs, 1H), 6.62 (d, 1H), 7.30 (m, 2H)].-   Step 2: 0.5 g (2.4 mmol)    Ethyl-(4-methoxy-benzo[d]isothiazol-3-yl)-amine was dissolved in 20    ml acetonitrile at room temperature. 0.76 g (9.6 mmol) pyridine    together with a catalytic amount of dimethylamino pyridine was    added, followed by 0.58 g (7.2 mmol) acetyl chloride. Stirring at    room temperature was continued overnight. Water was added and the    product was extracted with dichloromethane. The organic layer was    washed with aqueous HCl (10%), saturated sodium hydrogencarbonate    and water. The organic layer was dried over sodium sulfate. The    solvent was removed by distillation and the residue was purified on    silica (eluent: cyclohexane/ethyl acetate) to yield 0.47 g (1.88    mmol) of Compound example 5 (of table C)

S.4N-(4-Difluoromethoxy-benzo[d]isothiazol-3-yl)-N-ethyl-2,2,2-trifluoro-acetamide[Compound example 26 (of table C)]

-   Step 1: A mixture of 40 ml conc. HCl, 20 ml water and 20 ml ethanol    was cooled to 0-5° C. 10 g (37 mmol)    2-Cyano-3-difluoromethoxy-benzenesulfonyl chloride [WO 2006/56433]    were added to the stirred solution followed by 12.2 g (0.19 mol)    zinc powder in small portions. Stirring was continued at room    temperature for 2 h. Water and ethyl acetate were added and the    organic layer was dried over sodium sulfate. The solvent was removed    by distillation and the residue was purified on silica (eluent:    toluene/acetone) to yield 2.62 g (12 mmol)    2-Difluoromethoxy-6-mercapto-benzamide.-   Step 2: 2.1 g (9.6 mmol) 2-Difluoromethoxy-6-mercapto-benzamide was    dissolved in 90 ml methanol. A solution of 0.76 g potassium    hydroxide (85%) in 90 ml water was added. 1.6 g    hydroxylamine-O-sulfonic acid and 1.26 g potassium hydroxide (85%)    were dissolved in 90 ml water and the solution was added dropwise to    the reaction mixture at 0° C. Stirring was continued at 0° C. for    3 h. The reaction mixture was extracted 3 times with    dichloromethane. The aqueous layer was acidified with aq. HCl(10%)    and the product was extracted with dichloromethane. The organic    layer was dried over sodium sulfate. Evaporation of the solvent gave    1.2 g (4.4 mmol) 4-Difluoromethoxy-benzo[d]isothiazol-3-one (m.p.    176-177° C.)-   Step 3: 3.1 g (14 mmol) Difluoromethoxy-benzo[d]isothiazol-3-one was    dissolved in 100 ml dichloromethane at room temperature. 1.13 g (14    mmol) pyridine was added. 4.0 g (14 mmol) trifluoromethanesulfonic    anhydride was added dropwise. Stirring at room temperature was    continued for 2 h. Water was added and the product was extracted    with dichloromethane. The organic layer was washed with aqueous HCl    (10%), and water. The organic layer was dried over sodium sulfate.    The solvent was removed by distillation to yield 4.3 g    trifluoromethanesulfonic acid    4-difluoromethoxy-benzo[d]isothiazol-3-yl ester which was used for    the next step without further purification.-   Step 4: 0.5 g (1.4 mmol) 4-difluoromethoxy-benzo[d]isothiazol-3-yl    ester was dissolved in 20 ml tetrahydrofuran and 0.23 g    triethylamine was added. The solution was treated for 5 minutes with    gaseous ethylamine and stirred at room temperature for additional 30    min. Water was added and the product was extracted with ethyl    acetate. The organic layer was washed with aqueous potassium    carbonate (5%) and water. The organic layer was dried over sodium    sulfate. The solvent was removed by distillation and the residue was    purified on silica (eluent: cyclohexane/ethyl acetate) to yield 0.14    g (0.46 mmol)    (4-difluoromethoxy-benzo[d]isothiazol-3-yl)-ethyl-amine.-   Step 5: 0.8 g (3.4 mmol)    (4-Difluoromethoxy-benzo[d]isothiazol-3-yl)-ethyl-amine was    dissolved in 50 ml acetonitrile at room temperature. 1.1 g (13.4    mmol) pyridine together with a catalytic amount of dimethylamino    pyridine was added. A solution of 0.72 g (3.4 mmol)    trifluoroaceticacid anhydride in 20 ml acetonitrile was added    dropwise. Stirring at room temperature was continued for 4 h. Water    was added and the product was extracted with ethyl acetate. The    organic layer was washed with aqueous HCl (10%), and water. The    organic layer was dried over sodium sulfate. The solvent was removed    by distillation and the residue which was purified by treatment with    methyl tert. butylether to yield 0.35 g (1.03 mmol) compound example    26 (of table C).    B. Biological Examples of Action Against Pests

If not otherwise described, the active compounds were formulated in amixture of 50 vol.-% acetone:50 vol.-% water. A nonionic surfactant(Kinetic®) was included in the solution at a volume of 0.01% v/v.

In the following tests, the formulated solutions of the active compoundswere diluted to an active ingredient concentration of 300 ppm and thediluted solutions were applied in the below mentioned tests.

The action of the compounds of the formula I against pests wasdemonstrated by the following experiments:

B.1 Cotton Aphid (Aphis gossypii)

Cotton plants at the cotyledon stage were infested prior to treatment byplacing a heavily infested leaf from the main aphid colony on top ofeach cotyledon. The aphids were allowed to transfer overnight and thehost leaf was removed. The infested cotyledons were then dipped andagitated in the test solution for 3 seconds and allowed to dry in a fumehood. Test plants were maintained under fluorescent lighting in a 24-hrphotoperiod at 25° C. and 20-40% relative humidity. Aphid mortality onthe treated plants, relative to mortality on untreated check plants, wasdetermined after 5 days.

In this test compound examples 1-25, 27-59, 76-78, 80-83, 86, 87, 89,91, 92, 94, 96-103, 105, 106, 108, 115, 118 and 125 provided at 300 ppmat least 89% mortality of cotton aphid (Aphis gossypii, mixed lifestages) in comparison with untreated controls.

B.2 Green Peach Aphid (Myzus persicae)

Bell pepper plants at the first true-leaf stage were infested prior totreatment by placing heavily infested leaves from the main aphid colonyon top of the treatment plants. The aphids were allowed to transferovernight to accomplish an infestation of 30-40 aphids per plant and thehost leaves were removed. The infested leaves of the test plants werethen dipped and agitated in the test solution for 3 seconds and allowedto dry in a fume hood. Test plants were maintained under fluorescentlighting in a 24-hr photoperiod at 25° C. and 20-40% relative humidity.Mortality on the treated plants, relative to mortality on untreatedcheck plants, was determined after 5 days.

In this test compound examples 1-19, 25, 27-43, 44-52, 55-59, 76, 77,82, 83, 87, 89-91, 96-98, 100-103, 118 and 125 provided at 300 ppm atleast 89% mortality of green peach aphid in comparison with untreatedcontrols.

B.3 Cowpea Aphid (aphis craccivora)

The active compound is dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:acetone. The test solution isprepared at the day of use.

Potted cowpea plants colonized with approximately 100-150 aphids ofvarious stages were sprayed after the pest population has been recorded.Population reduction was assessed after 24, 72, and 120 hours.

In this test, compounds 76, 77, 81, 82, 87, 90-92, 94, 96-103, 105, 106,108 and 118 at 300 ppm showed over 89% mortality in comparison withuntreated controls.

B.4 Southern Armyworm (Spodoptera eridania), 2nd Instar Larvae

The active compounds were formulated in 50:50 acetone:water (vol) and100 ppm Kinetica™ surfactant.

A pair of first true leaves of Sieva lima bean was dipped into the testsolution and allowed to dry. The leaves were then placed in a plasticperforated zip enclosure bag and ten 2nd instar larvae were added. At 4days, observations were made of mortality and reduced feeding.

In this test, compounds 74, 75 and 113 at 300 ppm showed over 89%mortality in comparison with untreated controls.

B.5 Diamond Back Moth (plutella xylostella)

The active compound is dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water:acteon. The test solution isprepared at the day of use.

Leaves of Chinese cabbage were dipped in test solution and air-dried.Treated cabbage leaves were placed in petri dished lined with moistfilter paper and 3rd instar larvae were added. Mortality was recorded24, 72, and 120 hours after treatment.

In this test, compounds 105 and 113 at 300 ppm showed over 89% mortalityin comparison with untreated controls.

The invention claimed is:
 1. A compound of formula I

wherein n is 0; A is A³:

R⁹ is selected from the group consisting of C₁-C₆-alkoxy, C₁-C₁₀-alkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₃-C₁₀-cycloalkyl, phenyl, naphtyl and5- or 6-membered heteroaromatic or 3 to 7-membered saturated orpartially unsaturated heterocyclic groups containing 1, 2, 3 or 4unsubstituted or substituted heteroatoms selected from the groupconsisting of O, S, SO, SO₂, N, NH and N—C₁-C₆-alkyl as ring members,wherein the heterocyclic groups may additionally contain 1, 2 or 3C(═O)groups as ring members, wherein the aliphatic radicals may beunsubstituted, partially or fully halogenated and/or may carry one ormore radicals, independently of one another selected from the groupconsisting of CN, NO₂, C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl, C₃-C₁₀-cycloalkyland phenyl, it being possible for phenyl to be unsubstituted, partiallyor fully halogenated and/or to carry one or more substituents,independently of one another selected from the group consisting ofC₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, whereinthe ring members of the cyclic groups may be unsubstituted, partially orfully halogenated and/or may carry one or more radicals, independentlyof one another selected from the group consisting of CN, NO₂, NH₂,C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy, C₁-C₁₀-haloalkoxy,C₁-C₁₀-alkylthio, C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl,C₁-C₁₀-haloalkoxy, C₁-C₁₀-haloalkylthio, C₁-C₁₀-alkoxycarbonyl,(C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl andphenyl, it being possible for phenyl to be unsubstituted, partially orfully halogenated and/or to carry one or more substituents,independently of one another selected from the group consisting ofC₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R¹⁰ isselected independently from R¹²; R¹² is selected from the groupconsisting of OR^(d), NR^(a)R^(b), C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl,C₂-C₁₀-alkynyl, C₃-C₁₀-cycloalkyl, phenyl, naphthyl and saturated,partially or fully unsaturated or aromatic 5- to 7-membered heterocyclicgroups containing 1, 2, 3 or 4 heteroatoms selected from the groupconsisting of O, CO, S, SO₂, N, NH or N—C₁-C₆-alkyl, wherein the carbonatoms of all mentioned radicals and the ring members of the heterocyclicrings may be unsubstituted, partially or fully halogenated and/or maycarry one or more radicals, independently of one another each selectedfrom the group consisting of CN, OH, NO₂, NH₂,C₁-C₁₀-alkyl,C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy, C₁-C₁₀-haloalkoxy,C₁-C₁₀-alkylthio,C₁-C₁₀-alkylsulfinyl, C₁C₁₀-alkylsulfonyl, C₁-C₁₀-haloalkylthio,C₁-C₁₀-alkoxycarbonyl, (C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino,C₃-C₁₀-cycloalkyl, phenyl, 5-or 6-membered heteroaromatic rings andaromatic 8-, 9- or 10-membered fused heterobicyclic ring systemscontaining 1, 2, 3 or 4 heteroatoms selected from the group consistingof O, CO, S, SO₂, N, NH and N—C₁-C₆-alkyl, it being possible for each ofthe aromatic or heteroaromatic rings to be unsubstituted, partially orfully halogenated and/or to carry one or more substituents,independently of one another selected from the group consisting ofC₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy, C₁-C₁₀-haloalkoxy,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₂-C₁₀-haloalkenyl, C₂-C₁₀-haloalkynyl,CN, NO₂, NH₂, C₁-C₁₀-alkylthio, C₁-C₁₀-alkylsulfinyl,C₁-C₁₀-alkylsulfonyl, C₁-C₁₀-haloalkylthio, C₁-C₁₀-alkoxycarbonyl,C₁-C₁₀-alkylaminocarbonyl, C₁-C₁₀-dialkylaminocarbonyl,(C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl,C₃-C₁₀-halocycloalkyl, C₃-C₁₀-cycloalkylamino and C₁-C₁₀-alkylcarbonyl;R¹ is selected from the group consisting of CN, NO₂,NH₂,azido, halogen,sulfonylamino, sulfenylamino, sulfinylamino, C(═O)R^(c), C₁-C₁₀-alkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₃-C₁₀-cycloalkyl, C₁-C₁₀-alkoxy,C₁-C₁₀-alkylthio, (C₁-C₁₀-alkyl)amino, di(C₁-C₁₀-alkyl)amino,C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfenyl and C₁-C₁₀-alkylsulfonyl,wherein the carbon atoms of the C₃-C₁₀-cycloalkyl and the mentionedaliphatic radicals may be unsubstituted, partially or fully halogenatedand/or may carry one or more radicals, selected from the groupconsisting of CN, NO₂, NH₂, C₁-C₁₀-alkoxy, C₁-C₁₀-alkylthio,C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl, C₁-C₁₀-haloalkoxy,C₁-C₁₀-haloalkylthio, (C₁-C₁₀-alkoxy)carbonyl, (C₁-C₁₀-alkyl)amino,di(C₁-C₁₀-alkyl)amino, C₃-C₈-cycloalkyl and phenyl, it being possiblefor phenyl to be unsubstituted, partially or fully halogenated and/or tocarry one or more substituents, independently of one another selectedfrom the group consisting of C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl,C₁-C₁₀-alkoxy and C₁-C₁₀-haloalkoxy; R², R³ and R⁴ are independentlyfrom each other selected from the group consisting of hydrogen, halogen,azido, COR^(c), CN, NO₂, NH₂, C₁-C₁₀-alkyl, C₃-C₁₀-cycloalkyl,C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy, C₁-C₁₀-alkylthio, C₁-C₁₀-alkylsulfinyl,C₁-C₁₀-alkylsulfonyl, C₁-C₁₀-haloalkoxy, C₁-C₁₀-haloalkylthio,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, (C₁-C₁₀-alkyl)amino,di(C₁-C₁₀-alkyl)amino, sulfonyl, sulfonylamino, sulfenylamino andsulfanylamino; and wherein R^(a) and R^(b) are selected independentlyfrom each other from the group consisting of hydrogen, C₁-C₁₀-alkyl,C₃-C₁₀-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, aryl and aromatic,saturated, partially or fully unsaturated heterocyclic rings, andwherein the carbon atoms of all mentioned radicals may be unsubstitutedor partially or fully substituted by halogen or C₁-C₁₀-alkyl; R^(c) isselected from the group consisting of NH₂, C₁-C₁₀-alkyl, C₁-C₁₀-alkoxy,C₁-C₁₀-alkylamino, di(C₁-C₁₀-alkyl)amino, aryl and saturated, partiallyunsaturated or aromatic 3- to 7-membered heterocyclic ring, which maycontain as ring members 1, 2 or 3 unsubsituted or substitutedheteroatoms selected from the group consisting of O, S, SO, SO₂, N, NHand N—C₁-C₆-alkyl, and wherein the carbon atoms of all mentionedradicals may be unsubstituted or partially or fully substituted byhalogen or C₁-C₁₀-alkyl; R^(d) is selected from the group consisting ofhydrogen, C₁-C₁₀-alkyl, C₃-C₁₀-cycloalkyl, C₂-C₁₀-alkenyl,C₂-C₁₀-alkynyl, aryl and aromatic, saturated, partially or fullyunsaturated heterocyclic rings; or the enantiomers, diastereomers orsalts thereof.
 2. The compound of claim 1, wherein R¹ is selected fromthe group consisting of halogen, C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl,C₁-C₁₀-alkoxy and C₁-C₁₀-haloalkoxy.
 3. The compound of claim 1, whereinR¹ is selected from the group consisting of halogen, C₁-C₁₀-alkoxy andC₁-C₁₀-haloalkoxy.
 4. The compound of claim 1, wherein R¹ is selectedfrom the group consisting of fluoro, chloro, difluoromethoxy,dichloromethoxy, trifluoromethoxy and trichloromethoxy.
 5. The compoundof claim 1, wherein R², R³ and R⁴ are independently from one anotherselected from the group consisting of hydrogen, F, Cl, Br and I.
 6. Thecompound of claim 1, wherein R², R³ and R⁴ are independently from oneanother selected from the group consisting of hydrogen and fluoro. 7.The compound of claim 1, wherein R², R³ and R⁴ are hydrogen.
 8. Thecompound of claim 1, wherein, R⁹ is C₁-C₆-alkyl and R¹⁰ is selected fromthe group consisting of OR^(d), NR^(a)R^(b), C₁-C₁₀-alkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₃-C₁₀-cycloalkyl and phenyl, whereinthe radicals may be unsubstituted, partially or fully halogenated and/ormay carry one or more radicals, independently of one another eachselected from the group consisting of CN, NO₂, NH₂, C₁-C₁₀-alkoxy,C₁-C₁₀-alkylthio, C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl,C₁-C₁₀-haloalkoxy, C₁-C₁₀-haloalkylthio, C₁-C₁₀-alkoxycarbonyl,(C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl andphenyl, it being possible for phenyl to be unsubstituted, partially orfully halogenated and/or to carry one or more substituents,independently of one another selected from the group consisting ofC₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy and C₁-C₁₀-haloalkoxy. 9.The compound of claim 1, wherein R¹ is selected from the groupconsisting of halogen, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy and R², R³ andR⁴ are independently of one another selected from the group consistingof hydrogen, F, Cl, Br and I.
 10. The compound of claim 1, wherein R¹ isselected from the group consisting of halogen, C₁-C₆-alkoxy andC₁-C₆-haloalkoxy and R², R³ and R⁴ are hydrogen.
 11. The compound ofclaim 1, wherein, R¹ is selected from the group consisting ofC₁-C₆-alkoxy and C₁-C₆-haloalkoxy; R², R³ and R⁴ are independently ofone another selected from the group consisting of hydrogen, F, Cl, Brand I; and R⁹ is C₁-C₆-alkyl and R¹⁰ is selected from the groupconsisting of C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₁-C₁₀-alkoxy and C₃-C₁₀-cycloalkyl, wherein the carbon atoms of allmentioned radicals may be unsubstituted, partially or fully halogenatedand/or may carry one or more radicals, independently of one another eachselected from the group consisting of CN, NO₂, NH₂, C₁-C₁₀-alkoxy,C₁-C₁₀-alkylthio, C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl,C₁-C₁₀-haloalkoxy, C₁-C₁₀-haloalkylthio, C₁-C₁₀-alkoxycarbonyl,(C₁-C₁₀-alkyl)amino, di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl, phenyland a 5-or 6-membered heteroaromatic ring, it being possible for eachring to be unsubstituted, partially or fully halogenated and/or to carryone or more substituents, independently of one another selected from thegroup consisting of CN, NO₂, NH₂, C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl,C₁-C₁₀-alkoxy, C₁-C₁₀-haloalkoxy, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,C₁-C₁₀-haloalkenyl, C₂-C₁₀-haloalkynyl, C₁-C₁₀-alkylthio,C₁-C₁₀-alkylsulfinyl, C₁-C₁₀-alkylsulfonyl, C₁-C₁₀-haloalkylthio,C₂-C₁₀-alkoxycarbonyl, C₁-C₁₀-alkylaminocarbonyl,C₁-C₁₀-dialkylaminocarbonyl, (C₁-C₁₀-alkyl)amino,di-(C₁-C₁₀-alkyl)amino, C₃-C₁₀-cycloalkyl, C₃-C₁₀-halocycloalkyl,C₃-C₁₀-cycloalkylamino, and C₁-C₁₀-alkylcarbonyl.
 12. The compound ofclaim 1, wherein, R¹ is selected from the group consisting ofC₁-C₆-alkoxy and C₁-C₆-haloalkoxy; R², R³ and R⁴ are hydrogen R⁹ isC₁-C₆-alkyl and R¹⁰ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₆-cycloalkyl and phenyl, wherein the carbon atoms or thecarbocyclic ring of the radicals may be unsubstituted, partially orfully halogenated and/or may carry one or more substituents,independently of one another selected from the group consisting of CN,NO₂, NH₂, C₁-C₁₀-alkyl, C₁-C₁₀-haloalkyl, C₁-C₁₀-alkoxy,C₁-C₁₀-haloalkoxy, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₂-C₁₀-haloalkenyl,C₂-C₁₀-haloalkynyl, C₁-C₁₀-alkylthio, C₁-C₁₀-alkylsulfinyl,C₁-C₁₀-alkylsulfonyl, and C₁-C₁₀-haloalkylthio.
 13. A compositioncomprising a compound of claim 1, or the enantiomer, diastereomer orsalt thereof and at least one inert liquid and/or solid carrier.
 14. Anagricultural composition comprising a compound of claim 1, or theenantiomer, diastereomer or agriculturally useful salt thereof, and atleast one inert liquid and/or solid agriculturally acceptable carrierand, optionally, a surfactant.
 15. A method for combating or controllinginsects, arachnids or nematodes comprising contacting an insect,arachnid or nematode or their food supply, habitat or breeding groundswith a pesticidally effective amount of a compound of claim 1, or theenantiomers, diastereomers or salts thereof, or a composition comprisingsaid compound.
 16. The method of claim 15, wherein the animal pest isfrom the order Homoptera or Thysanoptera.
 17. A method for protectinggrowing plants from attack or infestation by insects, arachnids ornematodes comprising contacting a plant, or soil or water in which theplant is growing, with a pesticidally effective amount of a compound ofclaim 1, or the enantiomers, diastereomers or salts thereof, or acomposition comprising said compound.
 18. The method of claim 17,wherein the animal pest is from the order Homoptera or Thysanoptera. 19.A method for the protection of seeds from soil insects and of theseedlings' roots and shoots from soil and foliar insects comprisingcontacting the seeds before sowing and/or after pregermination with of acompound of claim 1, or the enantiomers, diastereomers or salts thereofor a composition comprising said compound.
 20. The method of claim 19,wherein the compound is applied in an amount of from 100 mg to 10 kg per100 kg of seeds.
 21. The method of claim 19, wherein the resultingplant's roots and shoots are protected.
 22. The method of claim 19,wherein the resulting plant's shoots are protected from aphids.
 23. Aseed treated with a compound of claim 1, or an agriculturally usefulsalt thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.